Best Vacation Homes in Winchester
Apartment
10.0(65 Reviews)
2 Bedrooms
1 Bath
6 Guests
900 ft²
Oceanfront
Fireplace/Heating
Ocean View
Balcony/Terrace
£155/Night
7 Nights - £1,083
Apartment
10.0(4 Reviews)
2 Bedrooms
2 Baths
5 Guests
1679.17 ft²
Parking
Internet
Child Friendly
Security/Safety
£148/Night
7 Nights - £1,033
Bed & Breakfast
9.8(57 Reviews)
1 Bedroom
1 Bath
Spa- Fireplace/Heating
Pool- Balcony/Terrace
£232/Night
7 Nights - £1,625
Cabin
10.0(55 Reviews)
1 Bedroom
1 Bath
4 Guests
800 ft²
- Balcony/Terrace
Pet Friendly
Kitchen- Parking
£148/Night
7 Nights - £1,035
House
10.0(2 Reviews)
4 Bedrooms
3 Baths
12 Guests
2109.73 ft²
- Balcony/Terrace
- Pet Friendly
- Parking
Air Conditioner
£296/Night
7 Nights - £2,074
Apartment
10.0(35 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
£112/Night
7 Nights - £784
Apartment
10.0(26 Reviews)
1 Bedroom
1 Bath
2 Guests
902 ft²
- Fireplace/Heating
- Ocean View
View- Pet Friendly
£155/Night
7 Nights - £1,086
Apartment
10.0(13 Reviews)
2 Bedrooms
1 Bath
2 Guests
280 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
£87/Night
7 Nights - £612
Winchester Luxury Rentals
House
5 Bedrooms
4 Baths
6 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
£1,638/Night
7 Nights - £11,464
House
10.0(1 Review)
1 Bedroom
1 Bath
5 Guests
10763.91 ft²
Skiing- Fireplace/Heating
- Balcony/Terrace
- View
£714/Night
7 Nights - £5,000
House
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
£645/Night
7 Nights - £4,514
House
2 Bedrooms
2 Baths
5 Guests
2000 ft²
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
£584/Night
7 Nights - £4,087
House
10.0(1 Review)
6 Bedrooms
5 Baths
12 Guests
4200 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
£528/Night
7 Nights - £3,695
Other
10.0(1 Review)
5 Bedrooms
4 Baths
12 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
£526/Night
7 Nights - £3,679
House
10.0(13 Reviews)
3 Bedrooms
1 Bath
6 Guests
1200 ft²
- Ocean View
- Balcony/Terrace
- View
- Pet Friendly
£443/Night
7 Nights - £3,098
House
10.0(4 Reviews)
3 Bedrooms
1 Bath
7 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
£435/Night
7 Nights - £3,044
Winchester Pet Friendly Vacation Rentals
RV Rental
10.0(10 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£121/Night
7 Nights - £844
House
10.0(1 Review)
1 Bedroom
1 Bath
4 Guests
796.53 ft²
- Pet Friendly
- Parking
- Internet
- Child Friendly
£159/Night
7 Nights - £1,114
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
4 Guests
400 ft²
- Pet Friendly
- Kitchen
- Parking
- Air Conditioner
£125/Night
7 Nights - £877
Apartment
9.0(1 Review)
1 Bedroom
1 Bath
4 Guests
398.26 ft²
- Pet Friendly
- Parking
- Internet
- Child Friendly
£195/Night
7 Nights - £1,364
RV Rental
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£99/Night
7 Nights - £695
Cottage
9.6(44 Reviews)
2 Bedrooms
1 Bath
6 Guests
820 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
£234/Night
7 Nights - £1,636
Cottage
9.6(23 Reviews)
2 Bedrooms
2 Baths
5 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£404/Night
7 Nights - £2,825
Apartment
1 Bedroom
1 Bath
4 Guests
400 ft²
- Pet Friendly
- Kitchen
- Parking
- Air Conditioner
£108/Night
7 Nights - £759
Winchester Large Vacation Homes
House
9.8(18 Reviews)
4 Bedrooms
2 Baths
10 Guests
1660 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
£223/Night
7 Nights - £1,563
Bed & Breakfast
9.6(50 Reviews)
6 Bedrooms
6 Baths
16 Guests
96.88 ft²
- Oceanfront
- Spa
- Skiing
- Fireplace/Heating
£280/Night
7 Nights - £1,963
House
9.2(25 Reviews)
3 Bedrooms
1 Bath
10 Guests
Hot Tub- Fireplace/Heating
- Pool
- Ocean View
£263/Night
7 Nights - £1,843
Bed & Breakfast
9.6(49 Reviews)
4 Bedrooms
4 Baths
10 Guests
234.12 ft²
- Fireplace/Heating
- Balcony/Terrace
- Parking
- Air Conditioner
£115/Night
7 Nights - £806
House
7.2(5 Reviews)
5 Bedrooms
3 Baths
11 Guests
2100 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
£392/Night
7 Nights - £2,745
New
Ski Chalet
5 Bedrooms
4 Baths
11 Guests
4400 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
£698/Night
7 Nights - £4,885
House
4 Bedrooms
1 Bath
12 Guests
1450 ft²
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
£357/Night
7 Nights - £2,496
House
4 Bedrooms
2 Baths
14 Guests
2000 ft²
- Fireplace/Heating
- Balcony/Terrace
Breakfast- Pet Friendly
£187/Night
7 Nights - £1,307
Why Choose Rent By Owner for your Winchester Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Winchester
When should you plan your Vacation Rentals stay?
Choosing the right time to visit this destination can enhance your experience, as seasonal variations in the region offer distinct advantages for travelers seeking relaxation or outdoor adventures.
Peak Season Highlights
Summer (June to August)
During the warm summer months, you'll enjoy longer daylight hours and mild temperatures, making it ideal for outdoor activities and exploring the scenic beauty of this destination.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
Fall (September to November)
Autumn transforms the area with vibrant foliage and crisp air, offering a picturesque setting perfect for scenic drives and outdoor adventures at the peak of the leaf-peeping season.
Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F
Off-Season Highlights
Winter (December to February)
While colder, winter offers a tranquil ambiance with opportunities for cozying up in your rental and enjoying the snowy landscape in this region's peaceful off-season.
Average Temperature Daytime: 20°F to 35°F - Nighttime: 5°F to 20°F
Spring (March to May)
In early spring, the area begins to emerge from winter, with fewer crowds and pleasant temperatures that are perfect for exploring and experiencing the natural renewal here.
Average Temperature Daytime: 45°F to 60°F - Nighttime: 30°F to 40°F
Weekly Weather Forecast for Winchester
How to Book Your Winchester Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Winchester
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a spacious outdoor patio or deck perfect for relaxing and entertaining
- Take advantage of a private backyard with lush greenery and scenic views
- Make use of outdoor grilling areas for delicious barbecues in the fresh air
- Benefit from easy access to nearby hiking trails and nature walks
- Relax by an outdoor fire pit during cool evenings under the stars
- Utilize a well-maintained lawn suitable for outdoor games and activities
- Experience peaceful mornings on a porch or veranda overlooking the area's natural beauty
Top Attractions Around Winchester
What attractions are nearby?
Within this charming destination, you can explore outdoor activities such as hiking and boating, or enjoy local cultural experiences that showcase the region’s natural beauty and welcoming community.
Family Activities
- Appalachian Trail Hike: Embark on a family-friendly hike along the scenic Appalachian Trail as it passes through the region, offering breathtaking views and outdoor adventure.
- Winchester Historical Society Museum: Explore local history and enjoy engaging exhibits that provide insight into this area's rich heritage, perfect for curious young visitors.
- Bass Pond Recreation Area: Spend a day by the water at Bass Pond, where you can enjoy swimming, picnicking, and peaceful nature walks with your loved ones.
- Outdoor Family Activities: Take advantage of the area’s numerous parks and trails designed for family fun, including playgrounds and easy walking routes suitable for all ages.
Adult Activities
- Winchester Town Recreation Department: Engage in outdoor activities and sports at this local facility, perfect for relaxing or staying active during your stay.
- Historical Walking Tours: Discover the area's rich history by exploring scenic routes that highlight Winchester’s cultural heritage and charming landmarks.
- Wildlife Watching at Pisgah State Park: Experience the region's natural beauty while spotting local wildlife in this nearby expansive park area.
- Local Art Galleries and Studios: Immerse yourself in regional art scenes by visiting galleries that showcase talented artists from here and beyond.
Other Places to Stay in Winchester, NH
Ashuelot
Winchester Travel Tips
How Can You Make the Most of Your Stay?
- Explore local outdoor activities: Take advantage of the region's natural beauty by engaging in outdoor pursuits such as hiking or fishing, which showcase the area's scenic landscapes right outside your vacation rental.
- Visit nearby cultural sites: Immerse yourself in the local history and culture by visiting attractions that offer insights into the destination’s unique heritage.
- Plan your trip around seasonal events: Check for seasonal festivals or celebrations in the area to enrich your stay and experience the vibrant community spirit.
- Choose a centrally located rental: Opt for accommodations that provide easy access to key points of interest, making it convenient to explore the best of what this destination has to offer.
Transportation Options
- Winchester Transportation Services: Local shuttle and taxi services offer convenient options for exploring the area and reaching your vacation rentals with ease.
- Public Transit: The regional bus system connects Winchester to nearby towns and cities, providing an affordable way to navigate this scenic region.
- Car Rentals: Renting a vehicle is recommended if you wish to explore more remote parts of the area or enjoy flexible travel during your stay.
- Private Transfers and Taxis: For added convenience, private transfer services are available to transport you directly from airports or other destinations to your vacation accommodation.
Local Customs Options
- Traditional New England Hospitality: You will notice a warm and welcoming attitude from locals, reflecting the area's deep-rooted community spirit and friendly customs.
- Seasonal Festivals and Events: Participating in local celebrations offers a glimpse into the region's vibrant culture, especially during seasonal festivals that highlight Winchester’s regional heritage.
- Respect for Nature and Outdoor Traditions: The area values outdoor activities and conservation efforts, so respecting natural spaces and local outdoor customs enhances your experience here.
- Local Art and Craftsmanship: Supporting regional artisans by exploring local galleries and craft fairs gives you an authentic taste of the area’s artistic traditions.
Frequently Asked Questions About Winchester?
1. What are the top vacation rentals in Winchester?
There are a lot of options in Winchester. If you plan on staying in the Winchester area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Winchester:
- Vikings Villages Resort
- Beautiful lake side get away, quiet, and peaceful.
- Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
- Charming 3 bedroom 2 bath Lakeside Cabin on Pristine Swanzey Lake
- Unique second floor Private Studio with Coded Locks
- Lakefront Orange Vacation Rental - Pet Friendly!
- Waterfront House on Private Lake - Tranquil Location and Amazing Sunsets
- Studio w/Trail Access ~ 10 Mi to Brattleboro!
- Cozy, Rustic Summer Cabin on Clean Lake
- Downtown apartment ideal location to everything
2. How many vacation rentals have private pools in Winchester?
There are 5 vacation rentals with private pools near Winchester. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Winchester are best for families?
If you are looking for a family-friendly vacation home in Winchester, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Winchester:
4. How many Rentbyowner vacation rentals are available in Winchester?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 160 in the Winchester area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Winchester.
5. What is the cancellation policy for vacation rentals in this area?
Cancellation policies vary depending on the individual property listing. It is important to review the specific cancellation terms provided by the property owner when making your booking to understand any fees or restrictions that may apply.
6. How do I find out about amenities and house rules before booking?
Details about amenities and house rules are typically included in the property listing. Be sure to read the full description and contact the owner if you have specific questions to ensure the accommodation meets your needs.
7. Are there any additional fees I should be aware of when booking here?
Additional fees, such as cleaning fees, service charges, or security deposits, are usually specified in the listing. Review all costs carefully before confirming your reservation to avoid surprises.
8. What is the check-in and check-out process for these vacation rentals?
Check-in and check-out times are set by each property owner and are detailed in the listing. Contact the host directly if you need flexible timings or have special requests to ensure a smooth arrival and departure.
9. How do I get support if I encounter issues during my stay?
Support is available through the property owner or local management team. For urgent matters, contact the designated support contact provided in your booking confirmation for prompt assistance.
Winchester Top Rated Vacation Rentals
Bed & Breakfast
9.0(105 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
£243/Night
7 Nights - £1,699
Hotel
8.9(177 Reviews)
10 Baths
333.68 ft²
Private Pool- Oceanfront
- Fireplace/Heating
- Pool
£232/Night
7 Nights - £1,623
Hotel
8.8(1003 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
£143/Night
7 Nights - £1,001
Hotel
8.8(1001 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
£152/Night
7 Nights - £1,067
£133/Night
7 Nights - £929
Hotel
8.6(1004 Reviews)
1 Bath
- Pool
- Breakfast
- Kitchen
- Parking
£113/Night
7 Nights - £790
£116/Night
7 Nights - £810
Hotel
8.6(214 Reviews)
1 Bath
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
£123/Night
7 Nights - £864
