Winchester vacation rentals

We found 308 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:May 29 - Jun 5

Image gallery for Retreat or Reunion Home with Grand Porch and Views of Mountain and Lake

The Monadnock Manse
9.8 out of 10, Exceptional, (101 reviews)
Exceptional
(101 reviews)

Retreat or Reunion Home with Grand Porch and Views of Mountain and Lake

Harrisville

9% off
Price is $819
$5,735 for 7 nights
All fees included
Retreat or Reunion Home with Grand Porch and Views of Mountain and Lake

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Find out more about Winchester

Why visit Winchester

  • Outdoor Adventures: Winchester offers numerous nature reserves, forests, and parks perfect for hiking, biking, and exploring the great outdoors.
  • Romantic Getaways: The serene ambiance and stunning scenery make Winchester an ideal destination for couples seeking a peaceful retreat.
  • Family-Friendly Atmosphere: The charming town features attractions suitable for all ages, making it a great spot for family vacations.
  • Diverse Accommodations: Choose from cozy cottages, stylish apartments, or private vacation homes to find your perfect home away from home.
  • Warm Summers: Enjoy the warm, humid summers that enhance the town's inviting atmosphere for outdoor activities.

Popular types of accommodation in Winchester

Planning a getaway to Winchester? You're in for a treat. From charming houses and cozy cottages to stylish apartments with high ceilings, there's a perfect rental waiting for you. Explore more options near Winchester, whether you're searching for a spacious house for rent or a comfortable bedroom apartment. Discover your ideal home away from home and make your trip unforgettable.

  • Houses: The top choice for visitors to Winchester, these homes offer spacious and comfortable accommodations for families or groups.
  • Apartments: A popular option for travelers seeking convenience and a home-like atmosphere, ideal for couples or solo adventurers.
  • Cottages: These quaint and cozy retreats provide a charming escape, perfect for a romantic getaway or a peaceful weekend.
  • Cabins: Offering a rustic ambiance, cabins are a favorite for nature enthusiasts looking to unwind in serene surroundings.
  • Chalets: A delightful choice for those wanting a unique and picturesque stay, blending comfort with a touch of alpine charm.**

Top attractions near Winchester

Winchester, New Hampshire, is a perfect destination for outdoor enthusiasts seeking scenic beauty and romantic getaways. Explore the numerous nature reserves, forests, and parks that offer adventure and eco-friendly experiences. Whether traveling solo, with family, or as a couple, you'll find a variety of attractions that capture the essence of outdoor exploration in this charming town.

  • Moody Center: A serene institute dedicated to personal growth and spiritual development, located 5 miles from Winchester. Visitors enjoy its peaceful ambiance and engaging workshops.
  • Thomas Aquinas College: This vibrant modern college 5 miles away offers an enriching academic atmosphere with a focus on liberal arts, complemented by lively campus events.
  • Pisgah State Park: A stunning national park just 5 miles from town, perfect for outdoor enthusiasts. Experience hiking trails, breathtaking scenery, and a variety of recreational activities.

Things to do recommended for couples

For a romantic getaway in Winchester, indulge in a luxurious round at Crumpin-Fox Golf Club, revel in live music at The Stone Church, or embrace outdoor adventure at Granite Gorge. Each destination offers a unique experience perfect for couples looking to create lasting memories together.

Things to do recommended for families

Families visiting Winchester can enjoy a day at the scenic Lake Winnepesaukee, perfect for swimming and picnicking. The nearby Winchester Historical Society offers engaging exhibits, and kids will love exploring the beautiful hiking trails in the surrounding forests.

Things to do recommended for groups

Experience the charm of New England Sweetwater Farm & Distillery for a romantic evening, hike the scenic Metacomet-Monadnock Trail for an adventurous outdoor day, and shop at the Vermont Marketplace for family-friendly entertainment and unique finds—all within a short drive from Winchester.

*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

When you're planning a trip—whether it's with a group, your family, or your pets, or if you're considering longer stays—be sure to prioritize your filters accordingly. Here are some helpful tips for booking on Vrbo.

  • Traveling to Winchester with a group: Think about how many bedrooms you'll require, as well as features like a fully equipped kitchen or outdoor areas for group gatherings. The good news is that you can easily filter for these options and many more on Vrbo.
  • Traveling to Winchester with young kids: Traveling with little ones can be quite a task. It's important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, thinking about how close you are to family-friendly attractions is a smart move.
  • Taking your pets with you to Winchester: For many, a family vacation isn’t truly fulfilling without their furry companion by their side. If you can relate, explore Vrbo listings that welcome pets. Most of these pet-friendly homes come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at ease.
  • Planning for a long term stay visiting Winchester: If you're in search of vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include amenities like parking, 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 delightful blend of outdoor adventures and serene spots perfect for a romantic getaway. Explore the charming city and its nearby neighborhoods, where you'll find family-friendly atmospheres and luxurious homes. Enjoy the relaxing ambiance as you take in the stunning scenery and embrace the warm, humid summers. Whether you're seeking adventure or tranquility, Winchester promises a memorable experience for every traveler.

  • Brattleboro: Located 10 miles from Winchester, Brattleboro is a vibrant city known for its rich artistic community and outdoor adventures. Visitors flock to Brattleboro for skiing and sports, with access to ski resorts and fields that cater to all skill levels. The surrounding geography features picturesque lakes, stunning mountains, and lush valleys, making it a perfect backdrop for outdoor enthusiasts. Notable attractions include local art galleries, theaters, and the serene Connecticut River, offering a mix of cultural experiences and natural beauty.
  • Keene: Situated 12 miles from Winchester, Keene is a charming city that draws travelers seeking outdoor adventures and scenic landscapes. Known for its recreational opportunities, Keene features ski fields and resorts for winter sports lovers, along with beautiful lakes and rolling hills for hiking and biking in warmer months. The city is also home to a modern college university, adding a youthful vibrancy to the area. Visitors can enjoy local events, farmers' markets, and a variety of restaurants showcasing regional cuisine, all against a stunning backdrop of nature.
  • Richmond: Nestled within the vicinity of Winchester, Richmond is a quaint village that emphasizes outdoor activities and scenic beauty. Known for its recreational areas, the village offers opportunities for skiing, with easy access to ski fields. Richmond's landscape is highlighted by beautiful lakes, the nearby national state park, and majestic mountains, making it an ideal destination for nature lovers. Whether you're hiking, skiing, or simply enjoying the tranquil surroundings, Richmond provides a peaceful retreat for those looking to immerse themselves in 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 simple

Looking to cut costs on your next trip? Consider being flexible with your travel dates, as this can lead to significant price differences. Also, extending your stay can result in even better savings. To discover the ideal Vrbo property that fits your budget, make use of our filters to search by price, location, and type of vacation rental.

Unlock savings with One Key

Plan your group getaway by booking an eligible Vrbo, and you’ll earn OneKeyCash on your reservation. Being the organizer certainly has its perks. When you join our travel rewards program, One Key, you’ll gain immediate access to member discounts and have the opportunity to earn and redeem OneKeyCash on qualifying bookings. Sign up now and begin enjoying your savings.

Vrbo Trips: Effortless planning

Vrbo's cutting-edge Trip Board offers you a convenient way to plan your travel. You can start new trips, pick up right where you left off, or easily view and organize your travel plans. All the properties you've saved or booked before are now neatly categorized under Potential, Upcoming, or Current Trips. To explore the 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)
  • Friendly Farm (17.6 mi / 28.3 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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