Smallwood vacation rentals

We found 920 vacation rentals — enter your dates for availability

Discover a selection of 8 homes and other vacation rentals in Smallwood that are perfect for your trip. Vacation rentals offer the best amenities for your family, friends, or furry companion, like WiFi and a washer and dryer. You'll be able to choose a rental that has what everyone needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - Smallwood

Showing deals for:Sep 11 - Sep 18

Image gallery for Hemlock Estate: Indoor Hot Tub, Heated Pool, Game Room; Spacious, Ski & More!

Indoor spa tub
9.6 out of 10, Exceptional, (39 reviews)
Exceptional
(39 reviews)

Hemlock Estate: Indoor Hot Tub, Heated Pool, Game Room; Spacious, Ski & More!

Monticello

8% off
Price is $594
$4,160 for 7 nights
All fees included
Hemlock Estate: Indoor Hot Tub, Heated Pool, Game Room; Spacious, Ski & More!

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Find out more about Smallwood

Why visit Smallwood

  • Stunning outdoor scenery: Experience picturesque landscapes featuring beautiful lakes, rivers, and lush forests.
  • Outdoor activities: Engage in various adventures like hiking, fishing, and exploring serene forest reserves.
  • Charming accommodations: Stay in cozy vacation homes, cabins, and cottages that provide a relaxing retreat.
  • Local arts and culture: Discover nearby arts centers that showcase the creative spirit of the community.
  • Family-friendly atmosphere: Enjoy leisurely strolls and fun activities suitable for all ages.

Popular types of accommodation in Smallwood

Planning a getaway to Smallwood, NY? You're in for a treat. Discover the charm of Houses, cozy Cabins, and delightful Cottages that make this destination a favorite among travelers. Whether you’re searching for a quaint Casa Smallwood or luxurious villas in Smallwood, our selection of vacation rentals provides the perfect backdrop for your adventure. Start your journey to relaxation and exploration today.

  • Houses: The top choice for visitors to Smallwood, offering spacious accommodations perfect for families or groups.
  • Cabins: A close second, these rustic retreats are perfect for those seeking a connection with nature.
  • Cottages: Charming and intimate, these cozy spots are ideal for couples or solo travelers.
  • Chalets: A delightful option, providing a unique blend of comfort and mountain charm.
  • Apartments: Great for couples or solo travelers, these offer a home-like atmosphere with essential amenities.**

Top attractions near Smallwood

Smallwood, New York, offers a romantic getaway with stunning outdoor scenery. Visitors can explore beautiful lakes, rivers, and local arts centers, perfect for those seeking a beach experience or a peaceful retreat. Nearby attractions include top spots for outdoor activities and the serene forest reserve, making it an ideal destination for nature lovers and adventurers alike.

  • Bethel Woods Center For The Arts: A vibrant arts center that captures the cultural spirit of the region, featuring live performances, art exhibits, and beautiful outdoor spaces for relaxation and inspiration.
  • Woodstock Monument: A picturesque lake that offers a romantic setting with scenic views, perfect for outdoor activities like picnicking, swimming, and enjoying the beach vibes.
  • Mongaup River: A serene river that provides stunning scenery and opportunities for outdoor adventures like fishing, kayaking, and hiking along its banks.

Things to do recommended for couples

For a romantic getaway in Smallwood, enjoy a cozy lakeside picnic or take a scenic hike through the lush woods. Don’t miss a sunset stroll along the water, hand in hand, as you soak in the serene beauty of this charming destination.

Things to do recommended for families

Families visiting Smallwood can enjoy a day at the serene Smallwood State Park, perfect for hiking and picnicking. Kids will love the nearby water activities at Lake Smallwood, where fishing and kayaking are popular. Don't miss the charming local shops for unique souvenirs.

Things to do recommended for groups

Groups visiting Smallwood can enjoy a peaceful day at the nearby Smallwood State Park for hiking and picnicking, followed by a fun evening of local music and dining at nearby restaurants. Don't miss the chance to explore the charming local shops for unique souvenirs.

*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 Smallwood

If you’re traveling with a group, as a family, with pets, or planning for an extended stay, be sure to prioritize your preferences when filtering your options. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Smallwood with a group: Think about how many bedrooms you'll require and any additional features you might want, like a full kitchen or outdoor area for gatherings. Luckily, you can easily filter for these options and many more on Vrbo.
  • Traveling to Smallwood with young kids: Traveling with young children can be quite demanding. It's important to prioritize their comfort and safety, along with age-appropriate amenities like a private swimming pool. Additionally, think about how close you'll be to family-friendly attractions.
  • Taking your pets with you to Smallwood: For many families, a trip isn't truly complete without their furry companion. If that resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly properties offer amenities like feeding bowls and beds, ensuring that both you and your pet feel comfortable and at home.
  • Planning for a long term stay visiting Smallwood: If you're in search of vacation rentals offering discounts for month-long stays, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don't forget to include additional preferences like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay near Smallwood

Discover the charm of Smallwood, New York, where scenic views and a friendly atmosphere await. This quaint destination is perfect for a romantic getaway or an outdoor adventure, featuring lush landscapes, a small waterfall, and cozy vacation homes. Explore nearby neighborhoods that exude a trendy yet relaxing vibe, making it an ideal spot for family-friendly fun and leisurely strolls. Smallwood promises an unforgettable experience filled with warmth and picturesque beauty.

  • Monticello: Monticello, located a mere 7 miles from Smallwood, is a vibrant city that offers a delightful mix of family-friendly and romantic experiences. Visitors can enjoy exciting days at the local water park or indulge in rejuvenating body treatments. The city is also home to a variety of entertainment venues, including theaters and an event conference venue. With its proximity to attractions like theme parks, Monticello is a perfect destination for those seeking adventure and fun for all ages.
  • White Lake: Just 1 mile from Smallwood, White Lake is a charming city renowned for its romantic outdoor settings and picturesque scenery. Travelers can immerse themselves in the arts by visiting local theaters and arts centers, or enjoy live music concerts. The area is highlighted by its stunning lake views, historic sites, and nearby mountains, making it ideal for outdoor enthusiasts and those looking to relax in nature’s beauty. White Lake is a perfect spot for a serene getaway.
  • Bethel: Located 3 miles away from Smallwood, Bethel is steeped in culture and entertainment, attracting visitors with its romantic ambiance. The city features vibrant theaters and arts centers, serving as hubs for music concerts and cultural events. Surrounded by beautiful lakes, historic landmarks, and majestic mountains, Bethel offers a unique blend of entertainment and outdoor exploration. Whether you're looking to enjoy a night out or a day of hiking, Bethel provides a rich experience for every traveler.

Best time to go to Smallwood

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

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January24.3°F (-4.3°C)Light RainMostly CloudyAverageSlightly High
February26.2°F (-3.2°C)Light RainMostly CloudySlightly LowAverage
March33.6°F (0.9°C)Light RainMostly CloudyAverageSlightly Low
April45.1°F (7.3°C)Light RainMostly CloudyAverageSlightly Low
May56.5°F (13.6°C)Light RainMostly SunnyAverageAverage
June64.2°F (17.9°C)Light RainMostly SunnySlightly HighAverage
July70.2°F (21.2°C)Light RainMostly SunnySlightly HighSlightly High
August67.8°F (19.9°C)Light RainMostly SunnySlightly HighAverage
September61.5°F (16.4°C)Light RainMostly SunnyAverageAverage
October50.5°F (10.3°C)Light RainMostly SunnyAverageSlightly Low
November38.3°F (3.5°C)Light RainMostly SunnySlightly LowAverage
December30.2°F (-1.0°C)Light RainMostly CloudySlightly LowSlightly High

Booking with Vrbo is simple

Planning your next getaway and hoping to save some money? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, booking a longer stay can lead to substantial savings. To discover a Vrbo property that suits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a user-friendly platform where you can start planning new trips, resume your previous ones, or organize your travel arrangements. You'll easily find your saved or booked properties neatly categorized under Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Book a vacation rental for your Smallwood getaway

Learn about the unique charm of Smallwood with a stay in a private vacation home. You'll find plenty to explore during your stay in the area. A vacation rental can help make your stay complete. Many rentals come with a full kitchen and laundry facilities.

Activities and attractions in Smallwood

Are you searching for top things to see and do while you're in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Smallwood a one-of-a-kind vacation spot. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

  • Concord Monster Golf Course (8.9 mi / 14.4 km)
  • Sullivan County Golf and Country Club (10.3 mi / 16.5 km)
  • Holiday Mountain Ski and Fun Park (11 mi / 17.8 km)
  • Ski Big Bear at Masthope Mountain (13.8 mi / 22.2 km)
  • Monticello Motor Club (6.6 mi / 10.7 km)
  • Grossinger Country Club (10.4 mi / 16.7 km)

Exploring the natural features in Smallwood

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

  • Lake Superior State Park (3.3 mi / 5.2 km)
  • Woodstock Monument (4.5 mi / 7.2 km)
  • Mohican Lake (9.3 mi / 15 km)
  • Neversink River (12 mi / 19.3 km)
  • Lake Louise Marie (12.6 mi / 20.2 km)
  • Upper Delaware River (13 mi / 20.9 km)

Frequently asked questions

What is the best area to stay in Smallwood, New York, United States of America when booking a vacation rental?
When considering a vacation rental in Smallwood, New York, the charming neighborhood surrounding the Smallwood community is an excellent choice. This area is known for its serene atmosphere, making it superb for those looking to unwind amidst nature. The neighborhood features a variety of vacation rentals, ranging from rustic cabins to cozy cottages, allowing for a comfortable stay that suits different preferences.

One of the top attractions in the vicinity is the nearby Smallwood Lake, which offers opportunities for fishing, kayaking, and enjoying peaceful lakeside walks. Additionally, nature enthusiasts will appreciate the lush forests and hiking trails that surround the area, providing ample chances for outdoor exploration. The community also has a quaint, friendly vibe, making it easy for visitors to connect with locals and enjoy the relaxed pace of life here.
How much does it cost to rent a vacation home in Smallwood?
Prices for vacation rentals in Smallwood 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 Smallwood 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 Smallwood vacation house rentals?
You can find great discounts on house rentals in Smallwood 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 Smallwood?
For renting a beach house in Smallwood, travelers should focus on the picturesque area surrounding Smallwood Lake. This charming community offers a variety of vacation rentals that provide direct access to the lake, making it superb for those looking to enjoy water activities such as swimming, kayaking, and fishing. Many properties here feature amenities like private docks, spacious decks for outdoor dining, and fire pits for evening gatherings, enhancing the lakeside experience.

In addition, the nearby Bethel Woods Center for the Arts is a cultural highlight, where visitors can enjoy live music and events throughout the summer months. Rentals in Smallwood often come with conveniences such as fully equipped kitchens and comfortable living areas, ideal for families or groups seeking a relaxing getaway.
Where are the best Smallwood ski resort rentals?
For ski resort rentals near Smallwood, New York, travelers should consider options in nearby areas such as the Catskills and Sullivan County. While Smallwood itself is a quaint hamlet, the closest ski areas are in towns like Monticello and Liberty, which are just a short drive away. In Monticello, visitors can find a variety of vacation rentals, including cozy cabins and modern homes, many of which come equipped with amenities like fireplaces, full kitchens, and outdoor decks great for enjoying the natural surroundings.

In Liberty, look for accommodations that offer easy access to nearby ski slopes. These properties often feature comfortable living areas, ample sleeping space for families or groups, and convenient access to local dining and entertainment options. Many rentals also include practical amenities such as Wi-Fi, heating, and parking, making them ideal for winter getaways.

Additionally, the region offers beautiful scenery, with opportunities for snowshoeing and cross-country skiing nearby. The local community also hosts various winter events, adding to the charm of staying in this area. See all ski-in-/ski-out rentals in Smallwood.
What is the most popular type of vacation rental accomodation in Smallwood?
In Smallwood, cabins are the most popular vacation rental option, with about 13 available in the area. These rustic accommodations often feature cozy interiors, wood-burning stoves, and outdoor spaces for enjoying the serene surroundings. Additionally, several vacation houses and cottages can be found, providing a variety of options for travelers seeking more space. Many of these properties come equipped with fully stocked kitchens, living areas, and access to outdoor patios or decks great for relaxing after a day of exploring the picturesque landscape.
Are there any family house rentals in Smallwood?
In Smallwood, New York, there are some family-friendly house rentals available, with around 14 options to choose from. This charming community is great for families seeking a relaxing getaway. Many properties offer spacious living areas, full kitchens for preparing meals together, and outdoor spaces where children can play and enjoy the fresh air.

Visitors can explore the nearby natural beauty of the Catskill Mountains, which provide ample opportunities for hiking, fishing, and enjoying scenic views. The locale's peaceful atmosphere is complemented by easy access to local attractions, making it an inviting destination for families looking to create lasting memories.
Can I rent a vacation home with a pool or hot tub in Smallwood?
In Smallwood, New York, there are several vacation homes available for rent that feature pools and hot tubs. This picturesque area, located in the Catskills, offers a serene retreat for travelers looking to unwind. Many of these properties come equipped with private pools and hot tubs, providing the ideal setting for relaxation after a day of exploring the surrounding natural beauty.

In addition to the aquatic amenities, guests can expect spacious living areas, fully equipped kitchens for meal preparation, and outdoor spaces ideal for enjoying the fresh air.
Can I find long-stay vacation rentals in Smallwood?
A long-stay vacation rental in Smallwood 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 Smallwood?
In Smallwood, there are several pet-friendly house rentals available, providing a welcoming environment for travelers with furry companions. Many of these vacation rentals feature amenities such as fully equipped kitchens, spacious living areas, and private outdoor spaces, ideal for enjoying the serene surroundings.

The area is known for its beautiful natural scenery, making it superb for outdoor activities with pets. Nearby, you can find parks and walking trails that are suitable for leisurely strolls or hikes with your pet. These rentals often offer a cozy atmosphere, ensuring a comfortable stay while allowing you to explore the charming community and its picturesque landscapes.
Are there any remote work vacation rentals in Smallwood?
In Smallwood, New York, there are ample options for remote work vacation rentals, with around 20 available for travelers seeking a productive getaway. Many of these properties cater specifically to remote workers, featuring Wi-Fi and internet connections provided by third-party services, ensuring a reliable online presence. Additionally, you can expect amenities such as dedicated workspaces with desks and comfortable chairs, allowing for a conducive work environment.

The charming surroundings of Smallwood offer a peaceful atmosphere, superb for focusing on work while enjoying the beauty of nature. With nearby attractions like the scenic lakes and hiking trails, you can easily take breaks to recharge. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Smallwood vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Smallwood 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 Smallwood?
In Smallwood, popular vacation rental amenities include kitchens, allowing travelers to prepare their meals conveniently. Many properties also feature decks or patios, providing outdoor space to relax and enjoy the natural surroundings. Fireplaces are common in these rentals, adding a cozy touch, especially during cooler months. Onsite parking is typically available, making it easy for guests to come and go without hassle. Additionally, coffee and tea makers are often included, ensuring guests can enjoy their favorite warm beverages at any time.
When is the best time to visit Smallwood for a vacation rental?
The peak season for vacation rentals in Smallwood is from June to August, with July being the most popular month for visitors. This vibrant period attracts families and outdoor enthusiasts who flock to enjoy the beautiful scenery and various recreational activities available in the area. Expect warm temperatures in the 70s to low 80s Fahrenheit, great for hiking, fishing, and swimming in nearby lakes.

During the summer, Smallwood buzzes with energy as travelers indulge in outdoor adventures and community events. It's an ideal time to experience the local culture and connect with fellow vacationers while enjoying the lush, green landscapes.

If you're looking for a more budget-friendly option, consider visiting in December. While this month falls outside the typical tourist season, it offers a unique charm with its quiet atmosphere and winter scenery. Cozying up in a vacation rental during this time can provide a peaceful retreat, allowing you to enjoy a serene escape amidst the snow-dusted surroundings.
How early should I book a Smallwood vacation rental?
Book your Smallwood 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 Smallwood, New York, United States of America?
In Smallwood, New York, visitors can enjoy the serene beauty of the area, particularly the picturesque Smallwood Lake, which is superb for fishing, kayaking, and relaxing by the water. The nearby Catskill Mountains offer numerous hiking trails with varying levels of difficulty, providing opportunities for outdoor enthusiasts to explore the natural landscape. The community itself has a charming, rustic atmosphere with quaint cottages and a close-knit feel, making it ideal for a peaceful getaway. Additionally, the area is conveniently located near the Bethel Woods Center for the Arts, where visitors can catch live performances and cultural events.
Can I change or cancel my Smallwood home rental booking on Vrbo?
To find Smallwood 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 Smallwood 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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