Winchester holiday lettings

We found 314 holiday rentals — enter your dates for availability

Scroll through and select from holiday rentals in Winchester to find one that's perfect for your trip. Whether you're travelling with your children or with friends, holiday rentals have the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a pool. You'll be able to choose a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Winchester

Showing deals for:3 Jul - 10 Jul

Image gallery for Elegant Lodging in the Woods ~ Privacy & Comfort! Your Home Away from Home!

Come relax in NH with privacy and serenity. Super clean! Minutes to mountains.
10 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)

Elegant Lodging in the Woods ~ Privacy & Comfort! Your Home Away from Home!

Hillsboro

8% off
Price is £745
for 7 nights, 1 apartment
£106 per night
includes taxes & fees
Elegant Lodging in the Woods ~ Privacy & Comfort! Your Home Away from Home!

Find spaces that suit your style

Why visit Winchester

  • Outdoor Adventures: Embrace the stunning countryside with enchanting forests, tranquil lakes, and nature reserves, perfect for hiking and exploring.
  • Historic Attractions: Visit the historic Winchester Cathedral and embark on engaging town tours that reveal the area’s rich heritage.
  • Family-Friendly Atmosphere: Enjoy a serene environment with friendly locals, making it ideal for family getaways.
  • Charming Accommodations: Choose from a delightful range of holiday rentals, including cosy cottages and modern apartments.
  • Secluded Escapes: Discover nearby secluded spots for a truly memorable and romantic retreat.

Popular types of accommodation in Winchester

Discover a charming selection of Winchester holiday rentals, including houses, apartments, and delightful cottages. Whether you're seeking a cosy retreat in a traditional Winchester cottage or a modern apartment for your city adventures, we have the perfect accommodation to suit your needs. Enjoy transparency and savings as you explore our range of options for an unforgettable getaway in this historic city.

  • Houses: These are the top choice for visitors to Winchester, offering ample space and comfort for families or groups.
  • Apartments: A popular option for couples or solo travellers, providing a convenient and self-catering stay in the heart of the town.
  • Cottages: Quaint and charming, cottages offer a delightful escape with a touch of rustic charm.
  • Cabins: Perfect for those seeking a peaceful retreat, cabins provide a cosy atmosphere surrounded by nature.
  • Chalets: A unique lodging choice, chalets combine comfort with picturesque views, ideal for a scenic getaway.**

Top attractions near Winchester

Winchester, New Hampshire, offers a delightful escape for those seeking outdoor adventures, romantic getaways, and stunning scenery. Explore its enchanting forests, nature reserves, and tranquil lakes. Key attractions include the historic Winchester Cathedral, engaging tours of the town, the fascinating Winchester Science Centre, and the rich heritage of historic Winchester. This charming destination is perfect for eco-conscious travellers looking to immerse themselves in nature and adventure.

  • Thomas Aquinas College: A modern university offering a vibrant atmosphere, ideal for those interested in academic pursuits and engaging with a diverse student community.
  • Moody Center: An esteemed institute providing a serene environment, perfect for contemplation and reflection, catering to various educational and spiritual activities.
  • Historical Old NMH Campus Building #3: A historic building rich in culture, showcasing architectural beauty and serving as a reminder of the area's educational heritage.

Things to do recommended for couples

Seeking a romantic getaway in Winchester? Enjoy a luxurious round at Crumpin-Fox Golf Club, catch a lively performance at The Stone Church, or embrace adventure at Granite Gorge with skiing. Each experience offers a unique charm perfect for couples looking to create lasting memories.

Things to do recommended for families

Families visiting Winchester can explore the scenic hiking trails at Pisgah State Park and enjoy swimming or picnicking at Lake Warren. The local farmers' market offers a delightful taste of fresh produce, perfect for a family outing filled with delicious treats.

Things to do recommended for groups

Embark on an adventure along the Metacomet-Monadnock Trail for stunning views, shop for local goods at the Brattleboro Farmers' Market, and enjoy a film or performance at the Latchis Theatre, all within a short drive from Winchester.

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

If you're travelling with a group, as a family, bringing along pets, or seeking longer stays, be sure to filter your options according to your key priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Winchester with a group: Think about how many bedrooms you require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily refine your search to include all of these options, and much more, on Vrbo.
  • Traveling to Winchester with young kids: Travelling with young children can present its challenges. It’s important to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about your closeness to attractions that are family-friendly.
  • Taking your pets with you to Winchester: For many families, a holiday isn’t truly fulfilling unless their furry companion is along for the journey. If this resonates with you, take a look at Vrbo properties that welcome pets. Most 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 holiday rentals offering discounts for stays of a month or more, you’ve come to the perfect destination. By using 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 even a private pool in your search criteria.

Where to stay in and around Winchester

Winchester, New Hampshire, offers a delightful escape into stunning countryside, perfect for a relaxing and romantic getaway. The area is ideal for families, boasting friendly locals and a serene atmosphere. Explore the charming streets and immerse yourself in the beautiful scenery, where adventure awaits just beyond the quaint city. Nearby regions also provide a fantastic opportunity to experience secluded spots, making it a truly memorable destination for all types of travellers.

  • Brattleboro: Located 6.2km from Winchester, Brattleboro is a vibrant city known for its outdoor adventures and sports experiences. With the stunning backdrop of mountains and valleys, it’s a perfect destination for ski enthusiasts. Visitors can explore nearby ski fields and resorts, making it an ideal spot for winter sports. In addition to skiing, the area's lakes provide excellent opportunities for a range of water activities during the warmer months. The charming downtown area features local shops and eateries that reflect the town's artistic spirit.
  • Keene: Just 7.5km from Winchester, Keene is a picturesque city that invites outdoor lovers to immerse themselves in its scenic beauty. The surrounding mountains and lakes offer breathtaking views and ample opportunities for hiking, skiing, and other outdoor pursuits. The presence of a modern college university adds a youthful energy to the area, with various events and activities that attract visitors year-round. Keene’s downtown area is vibrant, featuring unique shops and delightful restaurants that showcase local flavours.
  • Richmond: Nestled within the Winchester area, Richmond is a quaint village that promises a delightful outdoor experience. It is surrounded by beautiful landscapes, including mountains and a national state park, making it a haven for nature lovers. Popular activities include skiing and exploring recreational areas, providing ample adventure for visitors. The village's serene atmosphere is perfect for those looking to relax and enjoy the scenic views of the local lakes and lush greenery.

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 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 a breeze

Looking to save on your next holiday? Consider being flexible with your travel dates, as this can lead to significant price differences. Furthermore, extending your stay often results in excellent savings. To discover the ideal Vrbo property that fits your budget, utilise our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's clever Trip Board offers you a dedicated space to plan new adventures, pick up right where you paused, or manage your travel arrangements. You can easily locate properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Take in the lakeside beauty of Winchester

The lake and forests provide a pleasant backdrop to your holiday home in Winchester. This city is relaxing and scenic, recognised for its canoeing, boating and kayaking. If you're looking for accommodation options with space to entertain friends and family, HomeAway 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 searching for top things to see and do in the city? Venture out of your holiday home and experience everything that makes Winchester a fun spot to go on holiday. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • 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 appreciate the scenery, Winchester is a great place to get outside. These are some of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • 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 holiday 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 holiday 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 holiday home in Winchester?
Prices for holiday 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 holiday 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 holiday 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 holiday rental accomodation in Winchester?
In Winchester, a variety of holiday 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 holiday rentals in Winchester?
A long-stay holiday 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 holiday rentals in Winchester?
In Winchester, New Hampshire, there are several remote work holiday 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 holiday rentals with parking?
Vrbo offers a wide selection of holiday 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 holiday rental?
The best time to visit Winchester for a holiday 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 holiday rental?
Book your Winchester holiday 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 holiday 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 holiday 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 holiday 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, 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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