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Winchester vacation rentals

We found 296 vacation rentals — enter your dates for availability

Scroll through and select from vacation rentals in Winchester to find one that's perfect for your trip. Whether you're traveling with a group or just with your pet, vacation rentals have the best amenities for spending time at your vacation home, which might include a garden and WiFi. You're sure to find a rental for everyone's needs, including places that are non-smoking or accessible.

Vacation rentals with weekly discounts - Winchester

Showing deals for:Nov 14 - Nov 21

Image gallery for Charming & Cozy River Front Cabin- Close to ski mountains. Ski,Fish,Swim & Hike!

Exterior detail
10 out of 10 rating
Exceptional
(16 reviews)

Charming & Cozy River Front Cabin- Close to ski mountains. Ski,Fish,Swim & Hike!

Brattleboro, VT

7% off
Price is CA $242
CA $2,331 total
includes taxes & fees
Charming & Cozy River Front Cabin- Close to ski mountains. Ski,Fish,Swim & Hike!

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Find out more about Winchester

Find out more about Winchester

Why visit Winchester

  1. Outdoor Adventures: Discover stunning forests, serene lakes, and beautiful nature reserves, perfect for hiking, fishing, and kayaking.
  2. Charming Downtown: Stroll through the quaint downtown area filled with friendly locals and unique shops.
  3. Romantic Getaways: Enjoy a peaceful retreat with opportunities for relaxation and romance in a picturesque setting.
  4. Diverse Accommodations: Choose from cozy cottages, private vacation homes, and modern apartments tailored to your needs.
  5. Family-Friendly Activities: Engage in various activities that cater to families, ensuring fun for all ages.

Popular types of accommodation in Winchester

Explore the charm of Winchester with our diverse vacation rentals, including houses, cozy cottages, and modern apartments. Whether you're seeking a peaceful retreat or a convenient base for your adventures, there's something for everyone. Discover the perfect Winchester cottage rentals or vacation homes that suit your needs, ensuring a memorable getaway in this beautiful Canadian destination.

  • Houses: The top choice for visitors in Winchester, these homes offer spacious living and comfort, ideal for families and groups.
  • Cottages: A charming option, cottages provide a quaint and cozy atmosphere for a relaxing getaway.
  • Apartments: Perfect for couples or solo travellers, these rentals offer convenience and easy access to local attractions.
  • Cabins: For those seeking a rustic experience, cabins offer a serene escape surrounded by nature.
  • Chalets: These mountain-style lodgings provide a unique and picturesque retreat for a memorable vacation.**

Top attractions in Winchester

Winchester, New Hampshire, is perfect for outdoor enthusiasts and those seeking a romantic getaway. Visitors can explore stunning forests, serene lakes, and beautiful nature reserves, making it an ideal spot for adventure and eco-friendly experiences. Whether you're travelling solo, with family, or as a couple, you'll find plenty of activities to enjoy the scenic beauty of this charming town and its surroundings.

  1. Thomas Aquinas College: A modern college with vibrant city vibes, offering a unique educational atmosphere just 8.0km from Winchester, perfect for those who appreciate contemporary architecture and academic life.
  2. Moody Center: An institute located 8.0km from Winchester, known for its welcoming environment and community-focused programs, ideal for visitors interested in learning about local initiatives.
  3. Historical Old NMH Campus Building #3: A historic building with rich cultural vibes, situated 8.0km away, showcasing beautiful architecture and a glimpse into the area's educational heritage.

Things to do recommended for couples

For a romantic getaway in Winchester, explore the luxury vibes at Crumpin-Fox Golf Club, enjoy live music at The Stone Church, or embrace the thrill of skiing at Granite Gorge. Each offers a unique experience for couples seeking adventure and relaxation together.

Things to do recommended for groups

Explore the stunning Metacomet-Monadnock Trail for a memorable hike, visit the vibrant Brattleboro Farmers' Market for local goods, and enjoy a show at the charming Latchis Theatre, perfect for a cultural family outing. These activities promise great experiences for your group in Winchester!

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

When planning your trip—whether you're travelling with a group, family, pets, or seeking longer accommodations—it's important to filter your options according to your top priorities. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to Winchester with a group: Think about how many bedrooms you'll require, as well as any amenities like a full kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Winchester with young kids: Traveling with young children can present its own set of challenges. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, considering how close you are to attractions that are enjoyable for families is a wise move.
  • Taking your pets with you to Winchester: For many families, a vacation isn’t truly fulfilling without their furry companion by their side. If that resonates with you, consider exploring Vrbo properties that welcome pets. Many of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Winchester: 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 utilizing the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Winchester

Winchester, New Hampshire, offers a delightful blend of outdoor adventures and scenic beauty, making it an ideal vacation destination. Whether you're exploring the charming downtown area or enjoying family-friendly activities nearby, you'll find a welcoming atmosphere filled with friendly locals. With opportunities for relaxation and romance, Winchester is perfect for those seeking both adventure and tranquility in a picturesque setting.

  • Brattleboro: Located approximately 16.1km from Winchester, Brattleboro is a vibrant city known for its outdoor adventures and sports experiences. This charming town is popular among travellers seeking skiing opportunities, with several ski fields and resorts nearby. The stunning natural landscape features picturesque lakes, majestic mountains, and serene valleys, making it an ideal destination for those who appreciate breathtaking scenery. Visitors can enjoy a variety of activities, from skiing in the winter to hiking and biking in the warmer months, ensuring a delightful experience year-round.
  • Keene: Situated about 19.3km from Winchester, Keene is a delightful city that offers a rich blend of outdoor adventures and scenic beauty. This area attracts those looking to explore ski fields and resorts while also providing access to stunning lakes and mountains. Keene is home to a modern college university, which adds a vibrant, youthful energy to the city. Whether you're hiking along beautiful trails or enjoying local events, Keene ensures a fulfilling travel experience surrounded by the splendour of nature.
  • Richmond: Nestled within the Winchester area, Richmond is a quaint village that beckons outdoor enthusiasts and nature lovers alike. This charming locale is perfect for those seeking adventure and stunning scenery, with recreational areas and ski fields readily accessible. Richmond's proximity to a national state park, along with its breathtaking lakes and mountains, provides ample opportunities for exploration. It's an excellent spot for a peaceful retreat where you can immerse yourself in the beauty of the great outdoors.

Best time to go to Winchester

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

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January23.2°F (-4.9°C)Light RainMostly SunnyAverageAverage
February25.2°F (-3.8°C)Light RainMostly SunnySlightly LowSlightly High
March32.9°F (0.5°C)Light RainMostly SunnyAverageSlightly Low
April45.0°F (7.2°C)Light RainMostly SunnyAverageSlightly Low
May57.0°F (13.9°C)Light RainMostly SunnyAverageAverage
June64.9°F (18.3°C)Light RainMostly SunnySlightly HighAverage
July71.2°F (21.8°C)Light RainMostly SunnySlightly HighSlightly High
August69.3°F (20.7°C)Light RainMostly SunnyAverageAverage
September61.9°F (16.6°C)Light RainMostly SunnySlightly HighSlightly Low
October50.5°F (10.3°C)Light RainMostly SunnyAverageAverage
November38.7°F (3.7°C)Light RainMostly SunnySlightly LowAverage
December29.7°F (-1.3°C)Light RainMostly SunnySlightly LowSlightly High

Booking with Vrbo is simple

Are you hoping to save on your upcoming trip? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, booking an extended stay can lead to substantial savings. To discover a Vrbo property that aligns with your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect option for your travels!

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides you with a convenient platform to plan new trips, manage ongoing arrangements, or review your bookings. Your saved or reserved properties are thoughtfully categorized into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Take in the lakeside beauty of Winchester

The lake and forests provide a pleasant backdrop to your vacation home in Winchester. This city is relaxing and scenic, recognized for its canoeing, boating and kayaking. If you're looking for accommodations with space to entertain friends and family, Vrbo has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Sightseeing in and around Winchester

Are you hoping to find attractions to see while you're in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that Winchester has to offer. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Northfield Mountain Recreation Center (12 mi / 19.3 km)
  • Brattleboro Country Club (12.2 mi / 19.6 km)
  • Scott Farm Orchard (13 mi / 21 km)
  • Brentwood Golf Course (14.9 mi / 23.9 km)
  • Monadnock State Park (15.8 mi / 25.4 km)
  • Granite Gorge (16 mi / 25.8 km)

Exploring the natural features in Winchester

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Winchester is a great place to get outside. Here are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city center:

  • Madame Sherri Forest (9.3 mi / 15 km)
  • Chesterfield Gorge Natural Area (9.8 mi / 15.8 km)
  • Spofford Lake (10 mi / 16.1 km)
  • Brattleboro Common (10.7 mi / 17.2 km)
  • Turner Falls (14.2 mi / 22.8 km)
  • Millers River (14.7 mi / 23.6 km)

Frequently asked questions

What is the best area to stay in Winchester when booking a vacation rental?
When considering a vacation rental in Winchester, New Hampshire, one of the most appealing areas to stay is near the charming downtown district. This area offers a delightful blend of local shops, cafés, and restaurants, making it a convenient base for exploring the town. Not far from here, you can visit the picturesque Ashuelot River, which is great for leisurely walks and enjoying the natural beauty of the surroundings.

Another lovely option is to stay closer to the scenic lake areas, such as Lake Monadnock. This region is known for its tranquil atmosphere and outdoor activities, including fishing and hiking. The lake provides a beautiful backdrop and is ideal for those looking to immerse themselves in nature. The number of vacation rental properties in these areas is varied, giving you a range of choices to suit different preferences and budgets.
How much does it cost to rent a vacation home in Winchester?
Prices for vacation rentals in Winchester 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 travelling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Winchester to more spacious homes.
Are there any discounts for Winchester vacation house rentals?
You can find great discounts on house rentals in Winchester 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 Winchester?
For renting a beach house in Winchester, New Hampshire, travellers should focus on the nearby areas of Lake Monomonac and the picturesque shores of the Connecticut River. Although Winchester itself is not directly on the coast, the region offers lovely lakefront properties that provide a tranquil escape. In the vicinity of Lake Monomonac, you'll find charming cottages and larger homes that often come equipped with amenities such as private docks, outdoor decks, and barbecue facilities, superb for enjoying summer afternoons by the water.

Properties around the Connecticut River, particularly near the town of Hinsdale, offer scenic views and easy access to water activities such as kayaking and fishing. Many of these rentals feature spacious living areas, full kitchens for self-catering, and outdoor spaces for dining al fresco or relaxing by the river. Families and groups can expect properties with multiple bedrooms and bathrooms, ensuring ample space for everyone.
Where are the best Winchester ski resort rentals?
For those seeking ski resort rentals near Winchester, New Hampshire, the closest skiing can be found at nearby areas such as Mount Snow and Stratton Mountain, both of which are a short drive away. In the village of West Dover, which is near Mount Snow, travellers can find a variety of rental properties including cosy chalets and modern condos. Many of these accommodations come equipped with essential amenities such as fully equipped kitchens, fireplaces, and sometimes hot tubs or saunas, providing a superb retreat after a day on the slopes.

In the Stratton Mountain area, visitors can explore a range of lodgings that cater to different group sizes, from intimate cabins to spacious townhouses. These rentals often feature ski-in/ski-out access, making it convenient for avid skiers. Additionally, amenities such as ski storage, laundry facilities, and communal areas enhance the overall experience.
What is the most popular type of vacation rental accomodation in Winchester?
In Winchester, a variety of vacation rentals are available, with cottages, apartments, and vacation houses being the most common types—each category featuring several options throughout the area. Cottages often provide a charming, rustic atmosphere, complete with fully equipped kitchens and cosy living spaces, making them superb for a relaxing getaway. Apartments tend to be centrally located, offering modern amenities and easy access to local shops and eateries. Vacation houses typically feature larger spaces, multiple bedrooms, and outdoor areas, ideal for families or groups looking to enjoy the beautiful New Hampshire surroundings.
Are there any family house rentals in Winchester?
In Winchester, New Hampshire, there are several family-friendly house rentals available, making it a lovely destination for those travelling with children. The area features spacious homes, often equipped with full kitchens, allowing families to prepare their own meals together. Many properties also come with outdoor spaces, superb for kids to play and enjoy the fresh air.
Can I find long-stay vacation rentals in Winchester?
A long-stay vacation rental in Winchester is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Winchester?
In Winchester, New Hampshire, there are several pet-friendly house rentals available for those looking to enjoy a getaway with their furry companions. Many of these properties feature amenities such as spacious yards, which provide ample space for pets to roam and play. Travellers can expect comfortable living areas, fully equipped kitchens, and outdoor spaces superb for relaxation or barbecues.
Are there any remote work vacation rentals in Winchester?
In Winchester, New Hampshire, there are several vacation rentals that cater specifically to remote workers. These properties typically offer essential amenities such as dedicated workspaces with desks and comfortable chairs, as well as reliable Wi-Fi to ensure a productive environment. Many rentals also provide tranquil settings, which are ideal for concentrating on work while enjoying the serene surroundings. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Winchester vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Winchester with parking available—perfect for families or travellers 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 Winchester?
In Winchester, popular vacation rental amenities include kitchens, which allow guests to prepare their meals, along with essential appliances such as dishwashers and microwaves for added convenience. Many properties also feature patios, providing a lovely outdoor space to relax and enjoy the surroundings. Additionally, some rentals come equipped with blenders, making it easy to whip up smoothies or other beverages.
When is the best time to visit Winchester for a vacation rental?
July is the most popular time to visit Winchester, New Hampshire, as the summer months from June to August see an influx of tourists eager to experience the town's natural beauty and outdoor activities. This peak season is superb for those who enjoy hiking in the picturesque White Mountains or exploring the many scenic lakes and parks in the area. Warm temperatures, typically in the mid to high 20s Celsius, create a comfortable environment for sightseeing, picnicking, and enjoying local festivals.

Visitors during July can expect a vibrant atmosphere, with various events and activities designed to entertain travellers. Whether you're kayaking on Lake Winchester or taking leisurely strolls through the charming town centre, the summer sun adds an extra touch of joy to your vacation experience.

For those looking for a more budget-friendly option, consider visiting in December. This month, while cooler with temperatures around freezing, offers a unique charm as Winchester transforms into a winter wonderland. Enjoy peaceful walks, festive decorations, and the opportunity for winter sports, making it a lovely time for a cozy retreat.
How early should I book a Winchester vacation rental?
Book your Winchester 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.
Can I change or cancel my Winchester home rental booking on Vrbo?
To find Winchester 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 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 travellers 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 cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Winchester 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.

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