Winchester vacation rentals

We found 310 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.

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Find out more about Winchester

Why visit Winchester

  • Outdoor Adventures: Winchester is perfect for nature lovers, offering stunning forests, parks, and nature reserves for exploration.
  • Scenic Beauty: Enjoy picturesque oak woodlands and serene landscapes that create a peaceful retreat.
  • Charming Accommodations: Choose from private vacation homes, cozy cottages, and apartments that make for an inviting stay.
  • Family-Friendly Atmosphere: The friendly neighborhoods and shopping options cater to visitors of all ages.
  • Romantic Getaway: Winchester's tranquil environment is ideal for couples seeking a memorable romantic experience.

Popular types of accommodation in Winchester

If you're planning a getaway to Winchester, you'll find a variety of excellent vacation rental options to suit your needs. Our most popular choices include houses, charming cottages, and cozy apartments. Many rentals offer inviting living rooms, pet-friendly policies, and even private pools for the ultimate relaxation. Discover the perfect home away from home and enjoy your stay in this beautiful destination.

  • Houses: The top choice for visitors to Winchester, these homes offer spacious and comfortable accommodations for families or groups.
  • Cottages: A delightful option for a quaint getaway, perfect for those seeking charm and coziness.
  • Apartments: Ideal for travelers looking for modern convenience and a central location during their stay.
  • Cabins: A favorite among nature enthusiasts, providing a rustic escape amidst serene surroundings.
  • Chalets: A unique lodging option offering a blend of comfort and alpine style, perfect for a memorable retreat.**

Top attractions in and around Winchester

Winchester, New Hampshire, offers a perfect getaway for outdoor enthusiasts and romantics alike. With its stunning forests, nature reserves, and parks, visitors can immerse themselves in eco-friendly adventures and enjoy the scenic beauty of the area. Whether you're looking for a peaceful retreat or an active exploration, Winchester's attractions cater to travelers seeking a memorable experience in nature.

  • Barden State Wildlife Management Area: This park offers a serene escape into nature with family-friendly trails, abundant wildlife, and eco-friendly activities, perfect for outdoor enthusiasts.
  • Spofford Lake: Located 10 miles away, this picturesque lake is ideal for romantic outings, featuring beautiful beaches and stunning scenery, perfect for swimming, picnicking, and relaxation.
  • Crumpin-Fox Golf Club: Also 10 miles from Winchester, this luxurious golf club boasts meticulously maintained greens and a beautiful landscape, providing an upscale experience for golf lovers.

Things to do recommended for couples

Planning a romantic getaway in Winchester? Enjoy a luxurious day at Crumpin-Fox Golf Club, just 10 miles away, or the scenic Brattleboro Country Club, 12 miles from town. Both offer stunning views and an ideal setting for couples to relax and connect.

Things to do recommended for families

Families visiting Winchester, New Hampshire, can explore the scenic trails at Pisgah State Park, enjoy a day of fun at Lake Warren, and visit local farms for hands-on experiences with animals. Don't miss the charming shops and eateries in the downtown area for a perfect family outing.

Things to do recommended for groups

Explore the scenic beauty of Lake Warren State Park, where your group can enjoy hiking and picnicking. Visit the historic Winchester Village, where you can stroll through charming shops and local eateries. Don't miss a guided tour of the local art galleries showcasing regional talent.

*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 Winchester

If you're planning a trip with a group, family, pets, or looking for extended stays, be sure to prioritize your filters accordingly. 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 you might want, like a full kitchen or outdoor space for gatherings. Luckily, you can easily filter for all these features and more on Vrbo.
  • Traveling to Winchester with young kids: Traveling with young kids can be demanding. It's important to prioritize their comfort and safety, along with finding suitable amenities like a private swimming pool. Additionally, looking for locations that are close to family-friendly attractions can enhance your experience.
  • Taking your pets with you to Winchester: For many families, a vacation wouldn't feel complete without their furry companions. If you can relate, explore Vrbo listings that welcome pets. Most of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that every member of your family feels comfortable and at home.
  • Planning for a long term stay visiting Winchester: If you're in search of vacation rentals offering discounts for month-long stays, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in and around Winchester

Winchester, New Hampshire, offers a charming blend of outdoor adventures and serene scenery perfect for a romantic getaway. Explore the picturesque oak woodlands and enjoy the friendly atmosphere that makes this rural setting inviting. Nearby, you’ll find family-friendly neighborhoods and shopping options that enhance your experience. Whether you seek relaxation or adventure, Winchester and its surroundings promise an unforgettable vacation filled with natural beauty and warm hospitality.

  • Brattleboro: Located approximately 10 miles from Winchester, Brattleboro is a vibrant city known for its outdoor adventure and sports experiences. Travelers flock to this picturesque locale for its ski fields and resorts, making it a winter sports haven. The surrounding natural beauty is accentuated by nearby lakes and mountains, providing a perfect backdrop for hiking and outdoor activities year-round. Not far from Brattleboro, you can explore the stunning landscapes of a national state park, ideal for both relaxation and adventure.
  • Keene: Situated around 12 miles from Winchester, Keene is a charming city that offers a delightful mix of outdoor activities and scenic beauty. Known for its accessible ski fields and resorts, Keene attracts those seeking adventure in the great outdoors. The area is rich in natural landmarks, including beautiful lakes and a prominent modern college university, which adds a youthful vibrancy to the town. Visitors can also venture to the nearby national state park, providing ample opportunities for exploration and recreation.
  • Richmond: Nestled within the vicinity of Winchester, Richmond is a quaint village that embraces the spirit of outdoor adventure. Perfect for skiing enthusiasts, the village offers easy access to ski fields and resorts, making it an ideal spot for winter sports. The local landscape is dotted with serene lakes and features a charming town hall that enhances its small-town appeal. Additionally, Richmond is close to a national state park, providing visitors with ample opportunities to engage with nature and enjoy 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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January23.2°F (-4.9°C)Light RainMostly SunnyAverageSlightly High
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 HighAverage
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 a breeze

Are you aiming to save money on your upcoming trip? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, booking for a longer duration 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.

Save more with One Key

Reserve an eligible Vrbo for your group getaway and earn OneKeyCash on your entire reservation. Being the organizer truly has its rewards. When you become part of our travel rewards program, One Key, you'll gain access to exclusive discounts and earn OneKeyCash on qualifying bookings. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning made easy

Vrbo's Trip Board offers an easy-to-use platform for planning your travel. You can create new trips, revisit previous ones, or manage your existing plans all in one place. Your saved or booked properties will be neatly organized into categories like Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/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:

  • Harris Hill Ski Jump (11.1 mi / 17.9 km)
  • Northfield Mountain Recreation Center (12 mi / 19.3 km)
  • Brentwood Golf Course (14.9 mi / 23.9 km)
  • Granite Gorge (16 mi / 25.8 km)
  • Shattuck Golf Course (16.4 mi / 26.5 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:

  • Swanzey Lake (6.4 mi / 10.4 km)
  • Madame Sherri Forest (9.3 mi / 15 km)
  • Madame Sherris Castle Ruins (9.4 mi / 15.1 km)
  • Chesterfield Gorge Natural Area (9.8 mi / 15.8 km)
  • Spofford Lake (10 mi / 16.1 km)
  • Wantastiquet Mountain (10 mi / 16.1 km)

Frequently asked questions

What is the best area to stay in Winchester, New Hampshire, United States of America when booking a vacation rental?
When looking for the best area to stay in Winchester, New Hampshire, consider the charming neighborhood near the town center. This area offers a delightful mix of local culture and easy access to essential amenities. You'll find a range of vacation rental options that cater to different preferences, from cozy cottages to more spacious homes.

One of the top attractions nearby is the historic Winchester Town Hall, which showcases beautiful architecture and is often used for community events. Additionally, the scenic Ashuelot River offers opportunities for outdoor activities such as kayaking and fishing, making it a great spot for nature lovers.
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 traveling 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. To get the best value, book early and take advantage of Vrbo's free rewards program.
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, travelers should consider the scenic areas around Lake Winnipesaukee, which is a popular destination for summer activities. The towns of Alton Bay and Wolfeboro, located near the lake, offer a variety of vacation rentals, including charming cottages and modern homes with waterfront access. Many properties in this region feature amenities such as private docks, outdoor decks, and spacious yards, superb for families looking to enjoy swimming, boating, and fishing.

In addition to the lake itself, the nearby Mount Washington Valley offers beautiful views and opportunities for hiking, adding to the allure of the area. Many rentals come equipped with kitchens, fire pits, and access to local attractions, ensuring a comfortable stay for visitors. The vibrant community around the lake also provides shops, restaurants, and festivals, making it an ideal spot for those seeking both relaxation and local culture.
What is the most popular type of vacation rental accomodation in Winchester?
In Winchester, cottages are a popular choice for vacation rentals, with several available throughout the area. These charming properties often feature cozy interiors, fully equipped kitchens, and outdoor spaces such as decks or yards, allowing guests to relax in a peaceful setting. Additionally, there are several apartments that provide convenient living arrangements, often equipped with modern amenities and easy access to local attractions. For those looking for a more adventurous stay, several campsites are also available, offering a chance to immerse oneself in the natural beauty of the region.
Are there any family house rentals in Winchester?
In Winchester, New Hampshire, there are several family-friendly house rentals available, making it an excellent choice for groups seeking a relaxing getaway. Many of these homes are situated in tranquil neighborhoods, offering spacious living areas and well-equipped kitchens that allow for convenient family meals. Visitors can also enjoy outdoor spaces, superb for children to play and for family gatherings.

The locale is just a short drive from local attractions like Lake Monomonac, where families can enjoy activities such as swimming, fishing, and hiking. Nearby, the charming town center provides opportunities for exploring unique shops and enjoying local cuisine.
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. 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 Winchester?
In Winchester, New Hampshire, there are several pet-friendly house rentals available, making it a great destination for travelers with pets. Visitors can expect a variety of amenities in these homes, including spacious backyards for pets to roam, fully equipped kitchens for convenient meal preparation, and cozy living areas great for relaxing after a day of exploring.

The area itself offers beautiful natural surroundings, ideal for outdoor activities with pets such as hiking and leisurely walks. Nearby, you can find picturesque spots like Lake Warren, where pets can enjoy the outdoors alongside their owners.
Are there any remote work vacation rentals in Winchester?
In Winchester, New Hampshire, travelers looking for remote work vacation rentals will find several options available. The area provides a tranquil setting ideal for productivity, with properties featuring dedicated workspaces, such as desks and comfortable chairs, alongside reliable internet access, including Wi-Fi. Many rentals also offer amenities for relaxation after work hours, like cozy living areas and outdoor spaces where you can unwind while enjoying the natural beauty surrounding the town. 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 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 Winchester?
In Winchester, popular vacation rental amenities include fully equipped kitchens, allowing travelers to prepare their own meals. Many properties also permit pets, making it convenient for those traveling with furry companions. Additional amenities often found in rentals include blenders for smoothies or other culinary creations, as well as decks or patios where guests can relax and enjoy the outdoors. Onsite parking is also commonly available, providing ease of access for those driving to the area.
When is the best time to visit Winchester for a vacation rental?
The peak season for visiting Winchester, New Hampshire, is during the summer months of June through August, with July being the most popular month. This vibrant period attracts travelers looking to enjoy outdoor adventures, scenic views, and local events. The warm weather, with temperatures typically ranging from the low 50s to mid-80s Fahrenheit, invites visitors to explore the area's natural beauty, including nearby lakes and hiking trails.

As you wander through Winchester, you'll discover a variety of activities tailored to those who appreciate both adventure and relaxation. The serene atmosphere of the region allows for leisurely strolls, fishing, and picnicking, making it an ideal spot for families and outdoor enthusiasts alike.

For those considering a more budget-friendly option, October presents a wonderful opportunity to experience the stunning autumn foliage that New England is famous for. The vibrant colors of the changing leaves create a picturesque setting for scenic drives and nature walks, all while avoiding the crowds of the summer months.

Ultimately, your choice of when to visit Winchester can shape your experience, whether you seek the lively ambiance of summer or the peaceful charm of fall.
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, New Hampshire, United States of America?
In Winchester, New Hampshire, visitors can explore a range of attractions that highlight the area's natural beauty and small-town charm. The Ashuelot River, which runs through the town, offers picturesque views and opportunities for fishing and kayaking. Nearby, the scenic Mount Monadnock provides hiking trails with breathtaking vistas, attracting outdoor enthusiasts from all around.

The historic Winchester Town Common is a lovely spot for a leisurely stroll, often featuring community events and gatherings. Additionally, the town's quaint downtown area has local shops and eateries that reflect the community's character.
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 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 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 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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