Roxbury vacation rentals

We found 420 vacation rentals — enter your dates for availability

Discover a selection of 17 homes and other vacation rentals in Roxbury that are perfect for your trip. Whether you're traveling with a group or just with your pet, vacation rentals have the amenities you need and want for your stay, such as air conditioning and WiFi. No matter what you're looking for, you'll be able to choose a rental to meet everyone's needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Roxbury

Showing deals for:Mar 27 - Apr 3

Image gallery for Lakewood Farmhouse with exceptional kitchen/ great room.

Great area to cook, dine, play board games.
10 out of 10, Exceptional, (19 reviews)
Exceptional
(19 reviews)

Lakewood Farmhouse with exceptional kitchen/ great room.

Pine Hill

9% off
Price is $586
$4,100 for 7 nights
All fees included
Lakewood Farmhouse with exceptional kitchen/ great room.

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Find out more about Roxbury

Why visit Roxbury

  • Outdoor Adventures: Enjoy skiing and a variety of outdoor activities in stunning natural landscapes.
  • Cultural Experiences: Immerse yourself in the local culture and history that Roxbury uniquely offers.
  • Charming Accommodations: Choose from cozy cabins, private homes, and charming cottages for a memorable stay.
  • Family-Friendly Atmosphere: Roxbury provides a relaxing environment perfect for families and nature lovers.
  • Serene Neighborhoods: Explore nearby neighborhoods for local amenities and a tranquil vibe.

Popular types of accommodation in Roxbury

Planning a getaway to Roxbury? You've picked a fantastic destination. Discover the charm of Roxbury vacation rentals, where you'll find a variety of options including houses, cozy cabins, and charming cottages. Whether you're searching for the perfect house rental or looking for the best amenities on Vrbo, Roxbury has something to suit every traveler's needs. Dive into your next adventure with confidence and ease.

  • Houses: The top choice for visitors, these homes offer a spacious and comfortable setting for families, groups, or couples seeking privacy and convenience in Roxbury.
  • Cabins: A cozy and rustic option, cabins provide an intimate experience, perfect for those who want to immerse themselves in nature while enjoying modern comforts.
  • Cottages: These charming and quaint accommodations are ideal for travelers looking for a peaceful retreat, often featuring unique character and local flair.
  • Chalets: Offering a blend of comfort and style, chalets are particularly popular among those seeking a mountain getaway with stunning views.
  • Apartments: A convenient choice for shorter stays, apartments provide all the essential amenities in a compact space, great for couples or solo travelers.**

Top attractions in and around Roxbury

Roxbury, New York, is the perfect destination for ski and adventure enthusiasts. With attractions like national parks and ski resorts, visitors can enjoy a range of outdoor activities while soaking in the beautiful scenery. Whether you’re seeking cultural experiences or just want to explore the great outdoors, Roxbury offers something for everyone, making it an ideal spot for a memorable vacation.

  • Plattekill Mountain: A premier ski resort offering thrilling winter sports, Plattekill Mountain is perfect for both seasoned skiers and beginners. Enjoy adventure-filled outdoor activities with stunning views of the surrounding landscape, making it a year-round destination.
  • Hobart Book Village: A charming and secluded attraction, Hobart Book Village is a haven for book lovers. Explore quaint shops filled with rare and used books, all while enjoying a relaxing atmosphere that invites you to unwind and read.
  • East Branch Delaware River: This picturesque river is ideal for outdoor enthusiasts. Enjoy scenic views, fishing, and kayaking amidst tranquil surroundings, making it a perfect spot for nature lovers to connect with the great outdoors.

Things to do recommended for couples

For a romantic getaway in Roxbury, hit the slopes at Plattekill Mountain for some skiing adventure. Afterward, enjoy a wine tasting at Windham Vineyards and Winery, just 14 miles away, for a perfect blend of romance and outdoor charm. Don't miss the thrill at Belleayre Mountain Ski Center, only 12 miles away.

Things to do recommended for families

Families will love the Pine Hill Community Center, located 12 miles from Roxbury. This recreation center offers wellness activities and relaxation, making it a perfect spot for quality family time and fun-filled experiences together.

Things to do recommended for groups

Groups traveling to Roxbury can enjoy a round of golf at Stamford Golf Club or Windham Country Club for an outdoor experience. For a unique twist, visit Union Grove Distillery to savor local spirits in a romantic setting, perfect for entertainment and relaxation.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Roxbury

If you're traveling with a group, your family, or even your pets, or if you're planning an extended stay, be sure to prioritize your filters accordingly. Here are some helpful tips for booking on Vrbo.

  • Traveling to Roxbury with a group: Think about how many bedrooms you require and any additional features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Roxbury with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you'll be to family-friendly attractions.
  • Taking your pets with you to Roxbury: For many families, a vacation just isn't the same without their furry companions. If this resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations come equipped with feeding bowls and cozy beds, ensuring that your entire family feels comfortable and at home.
  • Planning for a long term stay visiting Roxbury: If you’re in search of vacation rentals offering discounts for stays of a month or more, you’ve come to the right spot. By using the appropriate filters, you can easily discover and save on monthly rentals. Don’t forget to include features like parking, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Roxbury

Roxbury, New York, is a hidden gem perfect for a ski or adventure getaway. Surrounded by lush greenery and historical charm, this quaint city offers a relaxing atmosphere ideal for families and nature lovers alike. Explore nearby neighborhoods for local amenities and enjoy the serene vibes that make Roxbury a perfect destination for your next vacation. Whether you're seeking thrilling sports or peaceful retreats, you’ll find an unforgettable experience in this picturesque region.

  • Grand Gorge: Grand Gorge is a charming city located 6 miles from Roxbury, making it an ideal spot for adventure seekers. Renowned for its stunning ski fields and resorts, Grand Gorge offers a plethora of outdoor activities year-round. Visitors can explore the scenic mountains, relax by tranquil lakes, or hike through beautiful parks. Whether you’re hitting the slopes in winter or enjoying the breathtaking views in summer, Grand Gorge is a perfect destination for those looking to immerse themselves in nature and exhilarating outdoor experiences.
  • Denver: Situated also 6 miles from Roxbury, Denver is a vibrant city that attracts adventure lovers and sports enthusiasts alike. Known for its proximity to ski fields and resorts, this city offers thrilling winter sports and year-round outdoor activities. With stunning mountains, picturesque lakes, and access to national state parks, Denver is an outdoor playground. Travelers can indulge in skiing, snowboarding, and hiking, or enjoy local dining and cultural experiences. Denver is a fantastic base for anyone eager to explore the great outdoors while enjoying city amenities.
  • Prattsville: Located 7 miles from Roxbury, Prattsville is a quaint city that offers a blend of adventure and outdoor recreation. Like its neighboring cities, it boasts excellent ski fields and resorts perfect for winter sports. Prattsville is surrounded by majestic mountains and serene lakes, providing ample opportunities for hiking, fishing, and enjoying nature. The local parks add to the charm, making it a great spot for families and nature lovers. Whether you’re skiing down the slopes or exploring the picturesque surroundings, Prattsville promises an unforgettable outdoor experience.

Best time to go to Roxbury

If you're planning a trip to Roxbury, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from July to September, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January21.6°F (-5.8°C)Light RainMostly CloudyAverageSlightly High
February23.4°F (-4.8°C)Light RainMostly CloudyAverageSlightly High
March30.4°F (-0.9°C)Light RainMostly CloudyAverageAverage
April41.7°F (5.4°C)Light RainMostly CloudyAverageSlightly Low
May53.8°F (12.1°C)Light RainMostly CloudyAverageSlightly Low
June61.2°F (16.2°C)Light RainMostly SunnyAverageAverage
July66.9°F (19.4°C)Light RainMostly SunnySlightly HighAverage
August64.9°F (18.3°C)Light RainMostly SunnySlightly HighAverage
September58.3°F (14.6°C)Light RainMostly SunnySlightly HighSlightly Low
October47.7°F (8.7°C)Light RainMostly CloudySlightly LowAverage
November35.6°F (2.0°C)Light RainMostly CloudySlightly LowAverage
December28.0°F (-2.2°C)Light RainMostly CloudySlightly LowSlightly High

Booking with Vrbo is simple

Are you aiming to save on your upcoming travel plans? Being open to adjusting your travel dates can significantly impact prices, as they tend to vary. Additionally, if you opt for an extended stay, you often unlock substantial savings. To discover the perfect Vrbo property that fits your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We're here to help you find the best options.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your entire reservation. Being the planner truly has its perks. When you join our travel rewards program, One Key, you'll gain access to exclusive member discounts and earn OneKeyCash on eligible bookings. Sign up today and start enjoying your savings.

Vrbo Trips: Effortless planning

Vrbo's cutting-edge Trip Board offers you a convenient way to plan new trips, pick up right where you left off, and keep your plans organized. You can easily find the properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Book a vacation rental for your Roxbury getaway

Experience the unique character of Roxbury with a stay in a vacation home rental. There's no shortage of things to see and do in the area.Are you looking for specific amenities for your getaway? Many of our vacation rentals feature full kitchens and laundry facilities.

Sightseeing in and around Roxbury

Are you looking for top things to see and do in the city? Venture out of your cozy vacation rental and experience everything that makes Roxbury a fun place to get away. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Hunter Mountain (19 mi / 30.5 km)
  • Plattekill Mountain (4.5 mi / 7.2 km)
  • Hobart Book Village (7.4 mi / 12 km)
  • Belleayre Mountain Ski Center (11.5 mi / 18.5 km)
  • Pine Hill Community Center (12.5 mi / 20.1 km)
  • Windham Vineyards and Winery (13.7 mi / 22.1 km)

Exploring the natural landscape of Roxbury

Whether you're looking for fun outdoor activities or just want to take in the scenery, Roxbury is a great place to get out in nature. These are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city center:

  • East Branch Delaware River (11.3 mi / 18.1 km)
  • Canada Falls (12.3 mi / 19.8 km)
  • Belleayre Beach (13 mi / 20.9 km)
  • Catskill Mountains (22.3 mi / 35.9 km)
  • Relay State Forest (3 mi / 4.9 km)
  • Plattekill State Forest (4.9 mi / 7.8 km)

Frequently asked questions

What is the best area to stay in Roxbury when booking a vacation rental?
When planning a vacation rental in Roxbury, New York, one of the best areas to consider is the charming village center. This area offers a delightful blend of quaint shops, local eateries, and a welcoming community atmosphere. Staying here puts you within walking distance of top attractions such as the Roxbury Arts Group, which hosts various events and performances, and the picturesque Catskill Mountains, great for hiking, skiing, or simply enjoying the stunning scenery.

Another appealing option is the surrounding rural areas, where you can find a variety of vacation rentals that provide a serene escape from the hustle and bustle. Here, you'll have the opportunity to immerse yourself in nature, with easy access to outdoor activities like fishing and biking. The proximity to the beautiful nearby Merilac Park, known for its scenic trails and picnic spots, adds to the area's charm. Overall, Roxbury features a range of properties, from cozy cabins to spacious homes, suiting different preferences and group sizes.
How much does it cost to rent a vacation home in Roxbury?
Prices for vacation rentals in Roxbury vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Roxbury to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Roxbury vacation house rentals?
You can find great discounts on house rentals in Roxbury on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Roxbury?
For renting a beach house in Roxbury, New York, travelers should consider the picturesque area surrounding the nearby Ashokan Reservoir, where vacation rentals offer stunning views of the water and the surrounding Catskill Mountains. Properties in this region typically feature amenities like spacious decks for outdoor dining, fire pits for evening gatherings, and fully equipped kitchens that cater to families or groups looking to enjoy a serene retreat by the water.

While Roxbury itself is not a traditional beach destination, the proximity to the reservoir allows for various water activities, such as kayaking and fishing. Many rentals in this area come with private docks or easy access to public launch sites, enhancing the outdoor experience. Moreover, the charming town of Roxbury offers local shops, cafes, and eateries, providing convenience and a taste of local culture.

For those seeking a blend of relaxation and exploration, the nearby Catskill Park offers hiking trails and scenic vistas, with some properties featuring amenities like outdoor grills and fire pits, great for enjoying the natural beauty of the region.
Where are the best Roxbury ski resort rentals?
For the best ski resort rentals near Roxbury, New York, travelers should focus on the nearby Catskill Mountains, particularly in areas like Hunter and Windham. These towns provide a range of vacation rental options from cozy cabins to larger mountain lodges. Many properties come equipped with essential amenities such as full kitchens, fireplaces, and hot tubs, offering a comfortable retreat after a day on the slopes.

In Hunter, visitors can find rentals conveniently located near the ski lifts, allowing for easy access to the slopes. Local accommodations often include features like ski storage, outdoor decks with scenic views, and communal areas for relaxation. The vibrant atmosphere of Hunter also means that travelers have access to shops, restaurants, and après-ski activities.

Windham, located a short drive away, offers a slightly quieter vibe with rental properties that often boast picturesque mountain views. Many of these homes are designed with rustic charm, featuring wood-burning stoves, spacious living rooms, and outdoor spaces superb for enjoying the crisp mountain air.
What is the most popular type of vacation rental accomodation in Roxbury?
In Roxbury, vacation houses are the most popular rental option, with about 15 available throughout the area. These houses typically feature spacious living areas, multiple bedrooms, fully equipped kitchens, and outdoor spaces, making them ideal for families or groups looking for a cozy feel. Additionally, there are several cabins, cottages, and apartments that offer charming, rustic vibes, often located in nature, providing a cozy retreat for travelers. Chalets are also available, adding to the variety of unique accommodations that highlight Roxbury's picturesque surroundings.
Are there any family house rentals in Roxbury?
In Roxbury, New York, families will find a variety of vacation rentals—approximately 19 options available in the area. Nestled in the Catskill Mountains, the locale offers a charming atmosphere superb for family getaways. Many of these homes feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces ideal for children to play.

Visitors can enjoy amenities such as cozy fireplaces, Wi-Fi, and comfortable bedrooms, ensuring a pleasant stay for all ages. The surrounding area boasts beautiful landscapes, making it easy to explore nature through nearby hiking trails and outdoor activities. Additionally, Roxbury provides access to local attractions like the charming village center, where travelers can discover unique shops and eateries.
Can I rent a vacation home with a pool or hot tub in Roxbury?
In Roxbury, New York, there are several vacation homes available for rent that feature pools and hot tubs, making it a great choice for travelers seeking relaxation and leisure. The area is known for its picturesque mountain views and tranquil surroundings, which enhance the vacation experience. Many of these properties come equipped with private pools, hot tubs, and spacious outdoor areas superb for enjoying the natural beauty of the Catskills. Additionally, guests can expect amenities such as fully equipped kitchens for preparing meals, comfortable living spaces, and often outdoor seating for enjoying the serene environment.
Can I find long-stay vacation rentals in Roxbury?
A long-stay vacation rental in Roxbury is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Roxbury?
In Roxbury, there are several pet-friendly house rentals available, offering a variety of amenities for travelers. Many of these homes come equipped with spacious backyards, allowing pets to roam freely, as well as cozy interiors featuring modern kitchens, comfortable living areas, and sometimes even fireplaces for those chilly mountain evenings.

The area is surrounded by nature, making it ideal for outdoor enthusiasts and pet owners. Nearby, the Catskill Mountains provide numerous hiking trails where you can enjoy scenic views and explore the great outdoors with your furry friends. See all pet-friendly rentals in Roxbury.
Are there any remote work vacation rentals in Roxbury?
In Roxbury, New York, there are numerous remote work-friendly vacation rentals available, with around 18 options to choose from. This charming town, located in the beautiful Catskills, is ideal for those seeking a peaceful environment conducive to productivity. Many of these properties come equipped with essential amenities such as dedicated desks, ergonomic chairs, Wi-Fi, and laptop workspaces. Some even include additional features like computer monitors and safes for added convenience and security.

Beyond the work-friendly accommodations, Roxbury offers a picturesque setting with access to outdoor activities, including hiking trails and scenic views. The small-town atmosphere also provides a great backdrop for relaxation after a day of work, allowing travelers to unwind in nature or explore local shops and eateries. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Roxbury vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Roxbury with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Roxbury?
In Roxbury, popular vacation rental amenities include fully equipped kitchens, allowing travelers to prepare their own meals during their stay. WiFi is commonly available, providing connectivity for both leisure and work needs. Many rentals also feature a coffee and tea maker for a convenient morning brew. Additionally, outdoor spaces such as patios and decks are frequently included, offering guests a pleasant area to relax and enjoy the natural surroundings.
When is the best time to visit Roxbury for a vacation rental?
The best time to book a vacation rental in Roxbury is during the peak travel season, which spans from July to September. This vibrant period attracts visitors drawn to the area's stunning natural beauty and outdoor activities. August, in particular, stands out as the most popular month, offering warm temperatures ideal for hiking, biking, and exploring the charming local arts scene.

During the summer months, you can expect pleasant weather with temperatures typically ranging from the mid-60s to low 80s Fahrenheit. This comfortable climate makes it great for outdoor adventures, whether you're strolling through the picturesque village or embarking on hikes in the surrounding Catskill Mountains. The lush greenery and vibrant flora create a stunning backdrop for your explorations.

If you're looking for a more budget-friendly option, consider visiting Roxbury in November. This quieter month allows you to enjoy the tranquility of the area while experiencing the beauty of fall's final hues. While the outdoor activities may be less prevalent, the serene atmosphere is great for cozy getaways and exploring the local culture at a leisurely pace.

Ultimately, whether you prefer the lively summer scene or the peaceful autumn charm, Roxbury offers a variety of delightful experiences year-round.
How early should I book a Roxbury vacation rental?
Book your Roxbury vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Roxbury?
In Roxbury, visitors can enjoy a range of attractions that highlight the area's natural beauty and charming small-town atmosphere. The picturesque Roxbury Mountain Maple Sugar Farm offers a unique glimpse into the maple syrup production process, and it's a lovely spot to explore during the spring season.

The nearby Catskill Mountains provide ample opportunities for outdoor activities, including hiking, bird watching, and scenic drives, with many trails starting from the surrounding neighborhoods. The historic Roxbury Arts Group hosts various cultural events and exhibitions, making it a hub for local art and community engagement.

Additionally, the quaint Main Street features local shops, cafes, and eateries, reflecting the town's rustic charm. The nearby NYC Reservoirs are great for fishing and kayaking, providing a peaceful retreat for nature enthusiasts.
Can I change or cancel my Roxbury home rental booking on Vrbo?
To find Roxbury vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Roxbury vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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