Winchester vacation rentals

We found 318 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.

Holiday rentals with weekly discounts - Winchester

Showing deals for:Sept 11 - Sept 18

Image gallery for A Historic New England Farm Stay for Gatherings, Retreats & Reconnection

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8.0 out of 10, Very good, (5 reviews)
Very good
(5 reviews)

A Historic New England Farm Stay for Gatherings, Retreats & Reconnection

Temple

25% off
Price is CA $1,878
CA $16,350 total
includes taxes & fees
A Historic New England Farm Stay for Gatherings, Retreats & Reconnection

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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:

  • Northern Illusion (6.5 mi / 10.4 km)
  • Northfield Mountain Recreation Center (12 mi / 19.3 km)
  • Brattleboro Country Club (12.2 mi / 19.6 km)
  • Brentwood Golf Course (14.9 mi / 23.9 km)
  • Granite Gorge (16 mi / 25.8 km)
  • Ellinwood Country Club (16.8 mi / 27 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)
  • Madame Sherris Castle Ruins (9.4 mi / 15.1 km)
  • Spofford Lake (10 mi / 16.1 km)
  • Brattleboro Common (10.7 mi / 17.2 km)
  • Turner Falls (14.2 mi / 22.8 km)
  • Granite Gorge (16 mi / 25.8 km)

Frequently asked questions

What is the best area to stay in Winchester when booking a vacation rental?
When looking for the best area to stay in Winchester, New Hampshire, you might consider the charming neighbourhood near the town centre. This area offers a pleasant atmosphere with a mix of historical charm and natural beauty. While there may be a limited number of vacation rentals available, the properties here often provide easy access to local amenities and attractions.

One of the key highlights of staying in this vicinity is the proximity to Mount Monadnock, which is renowned for its hiking trails and stunning views. Additionally, the nearby Ashuelot River offers opportunities for fishing and kayaking, making it a lovely spot for those who appreciate outdoor activities.
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 Winchester ski resort rentals?
For skiing near Winchester, New Hampshire, the closest ski areas can be found at nearby resorts such as Monadnock Mountain or Pats Peak, both of which are within a reasonable driving distance. In the town of Keene, which is approximately 20 minutes away, travellers can find a range of vacation rentals that serve as convenient bases for skiing enthusiasts. Accommodations in this area typically include cosy cabins and modern apartments, many of which come with amenities like wood-burning stoves, fully equipped kitchens, and outdoor spaces for relaxation after a day on the slopes.

In addition to Keene, the quaint town of Jaffrey offers a selection of charming rental properties that often feature rustic decor and comfortable living areas, ideal for families or groups. Many homes here provide access to private outdoor areas, superb for enjoying the scenic landscape, and some may even include hot tubs for unwinding after a day of skiing.

The nearby Monadnock State Park is also a highlight for those looking to explore beyond the ski slopes, with hiking trails that offer stunning views of the surrounding mountains.
What is the most popular type of vacation rental accomodation in Winchester?
In Winchester, a variety of vacation rental accommodations are available, with cottages, apartments, and campsites being the most popular choices. Several cottages can be found in tranquil locations, providing a charming home-like atmosphere, often featuring amenities such as fully equipped kitchens, cosy living areas, and outdoor spaces for relaxation. Apartments are also prevalent, offering a comfortable stay with similar conveniences, ideal for couples or smaller groups. Additionally, several campsites cater to those looking for a more adventurous experience amidst nature.
Are there any family house rentals in Winchester?
In Winchester, New Hampshire, there are several family-friendly house rentals available, making it an attractive destination for those travelling with children. The area is known for its scenic beauty and outdoor activities, providing ample opportunities for family fun. Many of these homes offer spacious living areas, full kitchens for preparing family meals, and outdoor spaces where kids can play and explore.

Visitors can enjoy the nearby attractions, including the picturesque Lake Kanasatka, which is superb for swimming and fishing, as well as local hiking trails that cater to various skill levels. The charming town centre also features quaint shops and eateries, adding to the overall experience.
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 any remote work vacation rentals in Winchester?
In Winchester, New Hampshire, there are several remote work vacation rentals available, with around 12 options to choose from. These accommodations cater to those seeking a productive environment while enjoying the beauty of the region. Many properties come equipped with essential amenities such as free Wi-Fi, dedicated workspaces, and comfortable living areas, allowing for a seamless blend of work and relaxation.

The town itself is set amidst picturesque landscapes, offering opportunities for outdoor activities and exploration during breaks. Nearby attractions include scenic lakes and hiking trails, superb for unwinding after a day's work. 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 rental amenities include kitchens, which allow guests to prepare their own meals, as well as the option for pets to be permitted, making it a welcoming choice for those travelling with furry companions. Many properties also feature decks or patios, providing an outdoor space to relax and enjoy the scenic surroundings. For added convenience, onsite parking is commonly available, ensuring a straightforward stay. Some rentals may even include amenities like blenders for guests who enjoy making smoothies or other refreshments during their visit.
When is the best time to visit Winchester for a vacation rental?
The best time to visit Winchester for a vacation rental is during the peak season from June to August, with July being particularly popular among travellers. This vibrant summer period draws visitors eager to enjoy outdoor activities, local festivals, and the natural beauty that New Hampshire has to offer.

During these warmer months, you can expect pleasant temperatures ranging from the mid-teens to low 30s Celsius, ideal for hiking, boating, and exploring the picturesque scenery. The lush greenery and blooming wildflowers create a stunning backdrop for outdoor adventures, making it a fantastic time for families and friends to gather.

If you're looking for a more budget-friendly option, consider planning your visit in December. While this month falls outside the main tourist season, it offers a charming winter landscape superb for cosy getaways, with opportunities to enjoy seasonal festivities and the tranquillity of the snowy surroundings.

Ultimately, your choice may depend on whether you prefer the lively summer atmosphere filled with activities or the peaceful charm of winter in Winchester.
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.
What are the top attractions in Winchester?
In Winchester, New Hampshire, visitors can enjoy a variety of attractions that highlight the area's natural beauty and local history. The scenic Lake Monadnock is a popular spot for outdoor activities such as fishing, boating, and hiking, providing a tranquil escape for nature enthusiasts. The nearby Pisgah State Park offers extensive trails for hiking and biking, making it ideal for those who appreciate the great outdoors.

In the town centre, the historic Winchester Town Hall and the charming local shops provide a glimpse into the community's heritage. The annual events, such as the Winchester Farmers Market, showcase local produce and crafts, creating a vibrant setting for visitors.
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 cabin or a beach house, 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 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.
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.

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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, 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 organising 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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