Winchester holiday lettings

We found 324 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:16 Oct - 23 Oct

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

20% off
Price is £9,351
for 7 nights, 1 room
£1,336 per night
includes taxes & fees
A Historic New England Farm Stay for Gatherings, Retreats & Reconnection

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    Enjoy full kitchens, pools, gardens and more

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Why visit Winchester

  • Picturesque landscapes: Experience the stunning natural beauty of Winchester, with its lush forests and serene parks.
  • Charming village atmosphere: Explore the friendly Winchester Village, where locals create a warm and inviting environment.
  • Outdoor adventures: Enjoy eco-friendly activities such as fishing in tranquil lakes and hiking through scenic trails.
  • Historic town centre: Stroll through the historic centre, rich in character and charm, perfect for leisurely exploration.
  • Comfortable accommodation: Choose from delightful vacation rentals, including cosy cottages and well-appointed apartments.

Popular types of accommodation in Winchester

Welcome to Winchester, New Hampshire, a charming city brimming with picturesque landscapes and inviting experiences. Explore the serene beauty of local parks, enjoy fishing in tranquil lakes, or take a leisurely stroll through the historic town centre. For your stay, choose from a delightful array of vacation rentals, including private homes, cosy cottages, and well-appointed apartments, ensuring a comfortable retreat after a day of adventure. Discover the heart of New England in Winchester.

  • Houses: The top choice for visitors to Winchester, offering spacious and comfortable living for families or groups.
  • Cottages: A delightful option for those seeking a quaint and homely atmosphere, perfect for a peaceful retreat.
  • Apartments: Ideal for couples or solo travellers, providing a convenient and self-contained living space.
  • Cabins: A charming selection for nature enthusiasts, offering a rustic escape amid stunning landscapes.
  • Chalets: These are a wonderful choice for a unique stay, blending comfort with a touch of mountain charm.**

Top attractions near Winchester

Winchester, New Hampshire, offers a charming escape for outdoor enthusiasts and romantics alike, with its beautiful forests and nature reserves. Visitors can revel in the area's scenic parks, perfect for eco-friendly adventures. Whether you're exploring the tranquil surroundings or simply enjoying the natural beauty, Winchester provides a delightful backdrop for a memorable getaway.

  • Brattleboro Common: A charming urban park perfect for families, Brattleboro Common offers a relaxing environment with ample green space, ideal for picnics and outdoor activities amidst a vibrant community atmosphere.
  • Spofford Lake: This picturesque lake is renowned for its stunning scenery and tranquil beaches, making it an idyllic spot for romantic strolls, swimming, and enjoying nature’s beauty.
  • Stonewall Farm: A welcoming farm that embodies the spirit of community, Stonewall Farm is a delightful place to experience local agriculture, meet friendly animals, and participate in seasonal events.

Things to do recommended for couples

Winchester offers charming experiences for couples, such as a leisurely walk by Lake Ashuelot, where you can enjoy serene views. Don't miss the quaint local cafés for a cosy afternoon, or explore the scenic hiking trails nearby for a romantic adventure amidst nature.

Things to do recommended for families

Families visiting Winchester, New Hampshire can explore the wonders of nature at the beautiful Pisgah State Park, perfect for hiking and picnicking. Additionally, the local farmers' market offers a delightful taste of fresh produce and crafts, making it an enjoyable experience for all ages.

Things to do recommended for groups

Explore the scenic beauty of Pisgah State Park with hiking trails perfect for groups, or enjoy a leisurely day at Lake Warren for swimming and picnicking. Don't miss the local shops and eateries in the charming downtown area for a taste of Winchester's unique character.

*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 travelling with a group, family, or pets, or if you’re seeking longer stays, it's important to apply the right filters to meet your needs. Here are some helpful booking tips for using Vrbo.

  • Traveling to Winchester with a group: Think about how many bedrooms you'll require, along with amenities like a fully-equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for these options and much more on Vrbo.
  • Traveling to Winchester with young kids: Travelling with young children can be quite demanding. 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 family-friendly attractions.
  • Taking your pets with you to Winchester: For many, a family holiday wouldn’t be the same without their furry companion. If this resonates with you, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds to ensure 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 longer, 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 features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Winchester

Winchester, New Hampshire, offers a delightful escape for those seeking outdoor adventures and serene landscapes. Explore the charming Winchester Village, where friendly locals create a welcoming atmosphere. Enjoy romantic getaways amidst stunning scenery, perfect for leisurely strolls and picnics. Whether you're seeking adventure or a peaceful retreat, Winchester provides an idyllic setting to unwind and connect with nature, making it an excellent choice for a memorable holiday.

  • Brattleboro: Located a mere 16km from Winchester, Brattleboro is a vibrant city renowned for its outdoor adventures and sporting experiences. With its stunning ski fields and resorts, it draws visitors eager to embrace the thrill of winter sports. The region is also home to breathtaking natural landmarks, including picturesque lakes and mountains, as well as the expansive national state park perfect for hiking and exploration. Brattleboro's charming downtown features eclectic shops and delightful eateries, offering a perfect blend of nature and culture.
  • Keene: Situated approximately 19km from Winchester, Keene is celebrated for its outdoor pursuits and scenic landscapes that beckon nature enthusiasts. The city offers access to skiing opportunities, making it an ideal destination for those seeking adventure in the winter months. In addition to its ski resorts, Keene boasts a beautiful lake and the presence of a modern college university, adding a youthful vibrancy to the area. The nearby national state park provides ample opportunities for hiking, picnicking, and enjoying the great outdoors.
  • Northfield: Only 10km from Winchester, Northfield is a charming city that invites visitors to enjoy its outdoor and scenic offerings. Known for its educational institutions and private country clubs, the area presents a unique blend of recreation and relaxation. Golf enthusiasts will appreciate the local country club, while the nearby lake and modern college university provide opportunities for exploration and leisure. The visitor centre offers insights into the region's rich history and attractions, making Northfield a delightful stop on your journey.

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 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 hoping to save on your next journey? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, you can achieve noteworthy savings by opting for a longer stay. To discover a Vrbo property that suits your budget, utilise our filters to organise results by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's unique Trip Board offers you a dedicated space to plan new journeys, pick up from where you last stopped, or manage and organise your travel plans. You can now easily access properties you've saved or booked, categorised under 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:

  • 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)
  • Cathedral of the Pines (20.1 mi / 32.3 km)
  • Winchester Speedpark (2.6 mi / 4.2 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:

  • Bear Mountain State Forest (7.3 mi / 11.7 km)
  • Madame Sherri Forest (9.3 mi / 15 km)
  • Spofford Lake (10 mi / 16.1 km)
  • Wantastiquet Mountain (10 mi / 16.1 km)
  • Brattleboro Common (10.7 mi / 17.2 km)
  • Keene Forestry Park (10.8 mi / 17.4 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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