Estia Villas - Vacation Rentals in Winchester
Cabin
10.0
(
56 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
800 ft²
-
Parking -
Balcony/Terrace -
Kitchen -
Air Conditioner
US $274
/Night
7 Nights - $1,921
Apartment
10.0
(
5 Reviews
)
2 Bedrooms
2 Bathrooms
5 Guests
1679.17 ft²
-
Parking
-
Internet -
Child Friendly -
Security/Safety
US $199
/Night
7 Nights - $1,391
Bed & Breakfast
9.8
(
81 Reviews
)
1 Bedroom
1 Bathroom
-
Breakfast -
Parking
-
Kitchen
-
Air Conditioner
US $259
/Night
7 Nights - $1,810
New
Apartment
10.0
(
27 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
902 ft²
-
Parking
-
Ocean View -
View -
Kitchen
US $257
/Night
7 Nights - $1,797
House
10.0
(
15 Reviews
)
2 Bedrooms
2 Bathrooms
5 Guests
924 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $276
/Night
7 Nights - $1,929
Apartment
10.0
(
15 Reviews
)
2 Bedrooms
1 Bathroom
2 Guests
280 ft²
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $161
/Night
7 Nights - $1,124
RV Rental
10.0
(
14 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $186
/Night
7 Nights - $1,300
House
10.0
(
12 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
3200 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $502
/Night
7 Nights - $3,516
See More Winchester Vacation Rentals
Luxury Places to Stay in Winchester
Over 146+
Luxury Places to Stay in or Near Winchester
House
5 Bedrooms
4 Bathrooms
6 Guests
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $3,060
/Night
7 Nights - $21,422
House
10.0
(
1 Review
)
3 Bedrooms
2 Bathrooms
6 Guests
-
Air Conditioner
-
Internet
-
Child Friendly
-
Laundry
US $991
/Night
7 Nights - $6,940
House
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
5 Guests
10763.91 ft²
-
Parking
-
Skiing -
Balcony/Terrace
-
View
US $961
/Night
7 Nights - $6,730
House
8.0
(
2 Reviews
)
6 Bedrooms
5 Bathrooms
12 Guests
4200 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $845
/Night
7 Nights - $5,914
House
10.0
(
4 Reviews
)
3 Bedrooms
1 Bathroom
7 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $752
/Night
7 Nights - $5,263
House
10.0
(
13 Reviews
)
3 Bedrooms
1 Bathroom
6 Guests
1200 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $698
/Night
7 Nights - $4,889
Cabin
10.0
(
15 Reviews
)
3 Bedrooms
1 Bathroom
6 Guests
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $604
/Night
7 Nights - $4,229
House
10.0
(
11 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
3600 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $598
/Night
7 Nights - $4,188
See More Winchester Luxury Vacation Rentals
Find More Winchester Villas, Resorts, & Rentals on BedroomVillas
Top-Rated Vacation Rentals with a Pool in Winchester
Over 21+
Top-Rated Vacation Rentals with a Pool in or Near Winchester
Bed & Breakfast
9.8
(
59 Reviews
)
1 Bedroom
1 Bathroom
-
Breakfast
-
Parking
-
Pool -
Spa
US $324
/Night
7 Nights - $2,270
New
House
9.4
(
25 Reviews
)
3 Bedrooms
1 Bathroom
10 Guests
-
Hot Tub -
Parking
-
Pool
-
Ocean View
US $413
/Night
7 Nights - $2,894
Bed & Breakfast
9.0
(
106 Reviews
)
1 Bedroom
1 Bathroom
-
Breakfast
-
Parking
-
Pool
-
Balcony/Terrace
US $327
/Night
7 Nights - $2,287
US $168
/Night
7 Nights - $1,177
Hotel
8.8
(
180 Reviews
)
333.68 ft²
-
Private Pool -
Oceanfront -
Breakfast
-
Parking
US $312
/Night
7 Nights - $2,185
Hotel
8.6
(
1006 Reviews
)
-
Breakfast
-
Parking
-
Pool
-
Kitchen
US $146
/Night
7 Nights - $1,025
Hotel
8.6
(
1000 Reviews
)
-
Breakfast
-
Parking
-
Pool
-
Balcony/Terrace
US $205
/Night
7 Nights - $1,435
US $142
/Night
7 Nights - $993
Pet-Friendly Vacation Rentals in Winchester
Over 44+
Pet-Friendly Vacation Rentals in or Near Winchester
Apartment
10.0
(
2 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
400 ft²
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $221
/Night
7 Nights - $1,550
House
10.0
(
2 Reviews
)
4 Bedrooms
3 Bathrooms
12 Guests
2109.73 ft²
-
Parking
-
Balcony/Terrace
-
Air Conditioner
-
Internet
US $399
/Night
7 Nights - $2,792
Cottage
9.6
(
46 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
818 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $346
/Night
7 Nights - $2,422
Cottage
9.4
(
3 Reviews
)
3 Bedrooms
1 Bathroom
6 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $392
/Night
7 Nights - $2,741
House
7.2
(
5 Reviews
)
5 Bedrooms
3 Bathrooms
11 Guests
2100 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $569
/Night
7 Nights - $3,983
Apartment
1 Bedroom
1 Bathroom
4 Guests
400 ft²
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $277
/Night
7 Nights - $1,937
New
House
1 Bedroom
1 Bathroom
4 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $259
/Night
7 Nights - $1,815
RV Rental
1 Bedroom
1 Bathroom
6 Guests
-
Parking
-
Balcony/Terrace
-
Internet
-
Pet Friendly
US $81
/Night
7 Nights - $570
See More Pet-Friendly Vacation Rentals in Winchester on PetFriendly.io
Large Vacation Homes & Villas in Winchester
Over 11+
Large Vacation Homes & Villas in or Near Winchester
House
9.8
(
18 Reviews
)
4 Bedrooms
2 Bathrooms
10 Guests
1660 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $323
/Night
7 Nights - $2,258
Bed & Breakfast
9.6
(
50 Reviews
)
6 Bedrooms
6 Bathrooms
16 Guests
96.88 ft²
-
Oceanfront
-
Breakfast
-
Parking
-
Spa
US $377
/Night
7 Nights - $2,642
House
4 Bedrooms
1 Bathroom
12 Guests
1450 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $480
/Night
7 Nights - $3,360
House
4 Bedrooms
2 Bathrooms
14 Guests
2000 ft²
-
Breakfast
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $251
/Night
7 Nights - $1,759
House
10.0
(
2 Reviews
)
5 Bedrooms
4 Bathrooms
12 Guests
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $713
/Night
7 Nights - $4,991
Ski Chalet
5 Bedrooms
4 Bathrooms
11 Guests
4400 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $939
/Night
7 Nights - $6,576
House
7 Bedrooms
4 Bathrooms
14 Guests
-
Internet
-
Child Friendly
-
Laundry
-
Security/Safety
US $615
/Night
7 Nights - $4,307
House
7 Bedrooms
4 Bathrooms
15 Guests
-
Balcony/Terrace
-
Internet
-
Child Friendly
-
Laundry
US $615
/Night
7 Nights - $4,307
See More Family Vacation Rentals in Winchester on FVR
Wheelchair Accessible Vacation Homes in Winchester
Over 16+
Wheelchair Accessible Vacation Homes in or Near Winchester
Bed & Breakfast
10.0
(
2 Reviews
)
4 Bedrooms
4 Bathrooms
9 Guests
191.06 ft²
-
Parking
-
Balcony/Terrace
-
View
-
Kitchen
US $155
/Night
7 Nights - $1,085
US $201
/Night
7 Nights - $1,407
Hotel
9.1
(
203 Reviews
)
419.79 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $156
/Night
7 Nights - $1,089
Hotel
9.6
(
663 Reviews
)
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $165
/Night
7 Nights - $1,155
Hotel
8.5
(
248 Reviews
)
-
Private Pool
-
Breakfast
-
EV Charge Station -
Parking
US $325
/Night
7 Nights - $2,275
Hotel
8.8
(
785 Reviews
)
-
Breakfast
-
Parking
-
Kitchen
-
Air Conditioner
US $174
/Night
7 Nights - $1,220
US $218
/Night
7 Nights - $1,529
US $140
/Night
7 Nights - $983
Winchester Vacation Rentals and Airbnb Places to Stay Under $200
Over 46+
Winchester Vacation Rentals and Airbnb Places to Stay Under $200
Apartment
10.0
(
65 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
900 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $199
/Night
7 Nights - $1,394
Bed & Breakfast
9.6
(
49 Reviews
)
4 Bedrooms
4 Bathrooms
10 Guests
234.12 ft²
-
Parking
-
Balcony/Terrace
-
Air Conditioner
-
Internet
US $155
/Night
7 Nights - $1,085
US $151
/Night
7 Nights - $1,056
Apartment
10.0
(
37 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $172
/Night
7 Nights - $1,204
Apartment
2 Bedrooms
1 Bathroom
4 Guests
1225 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $99
/Night
7 Nights - $692
Apartment
2 Bedrooms
1 Bathroom
3 Guests
-
Kitchen
-
Air Conditioner
-
Internet
-
Pet Friendly
US $85
/Night
7 Nights - $593
Apartment
4.9
(
33 Reviews
)
1 Bedroom
1 Bathroom
3 Guests
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Pet Friendly
US $144
/Night
7 Nights - $1,008
Cabin
10.0
(
13 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
280 ft²
-
Parking
-
Spa
-
Ocean View
-
Balcony/Terrace
US $152
/Night
7 Nights - $1,063
See More Winchester Vacation Rental Deals
Instantly Bookable Vacation Homes in Winchester
Over 31+
Instantly Bookable Vacation Homes in or Near Winchester
House
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
5 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $311
/Night
7 Nights - $2,180
House
10.0
(
1 Review
)
2 Bedrooms
2 Bathrooms
5 Guests
924 ft²
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
US $331
/Night
7 Nights - $2,315
Apartment
9.8
(
7 Reviews
)
2 Bedrooms
2 Bathrooms
5 Guests
1684 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $239
/Night
7 Nights - $1,672
Cabin
9.6
(
34 Reviews
)
3 Bedrooms
1 Bathroom
4 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $289
/Night
7 Nights - $2,023
House
9.0
(
2 Reviews
)
2 Bedrooms
1 Bathroom
5 Guests
825 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $315
/Night
7 Nights - $2,206
House
7.4
(
3 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1600 ft²
-
Parking
-
Spa
-
Ocean View
-
Balcony/Terrace
US $397
/Night
7 Nights - $2,780
House
3 Bedrooms
1 Bathroom
6 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $470
/Night
7 Nights - $3,287
Ski Chalet
1 Bedroom
1 Bathroom
4 Guests
680 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $341
/Night
7 Nights - $2,389
About Winchester Vacation Rentals
With more than 155 Winchester vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Estiavillas and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Winchester.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Estiavillas Winchester, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Winchester. Places to stay near Winchester are 842.77 ft² on average, with prices averaging US $311 a night.
Estiavillas makes it easy and safe to find and compare vacation rentals in Winchester with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Top Rental Accommodation Types in Winchester
| Type | Count |
|---|---|
| Vacation Homes | 59 |
| Holiday Apartments | 31 |
| Hotels | 31 |
| B&B | 9 |
| Cottages | 8 |
| Cabin Rentals | 7 |
| Ski Chalet Rentals | 3 |
| Others | 2 |
| Resorts | 1 |
Use these Quick Filters to Find a Vacation Rental in Winchester
★ Pro Tip: Estiavillas makes it easy to compare the best listings on Estiavillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Estiavillas homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Winchester.
Weather in Winchester
View the weather forecast for Winchester before booking your Winchester Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Winchester, NH
Estiavillas offers a large selection of top attractions around Winchester. Research things to do on your vacation before you visit Winchester.
Keene State College
Spofford Lake
Deerfield Academy
Greenfield Community College
Northfield Mount Hermon School
Brattleboro Bowl
Turner Falls
Bridge of Flowers
Landmark College
Magic Wings Butterfly Conservatory
Asbury United Methodist Church
The Putney School
Monadnock State Park
Brattleboro Outlet Center
Brattleboro Farmers' Market
Granite Gorge
Colonial Theatre
The Stone Church
Brattleboro Country Club
Winchester Vacation Rental Frequently Asked Questions
How many vacation rentals have private pools in Winchester?
There are 3 vacation rentals with private pools near Winchester. Top-rated homes that have access to a swimming pool include:
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:
How many vacation rentals are available in Winchester?
Currently, the total number of properties listed in 2026 is over 155 in the Winchester area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Winchester.
