Estia Villas - Vacation Rentals in Winchester
Apartment
10.0
(
61 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
900 ft²
-
Parking -
Kitchen -
Air Conditioner -
Internet
US $289
/Night
7 Nights - $2,020
Apartment
10.0
(
2 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
301.39 ft²
-
Hot Tub -
Parking
-
Balcony/Terrace -
View
US $1,447
/Night
7 Nights - $10,127
House
1 Bedroom
1 Bathroom
-
Parking
-
Balcony/Terrace
-
Internet
-
Child Friendly
US $712
/Night
7 Nights - $4,981
House
10.0
(
33 Reviews
)
5 Bedrooms
3 Bathrooms
10 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $750
/Night
7 Nights - $5,251
House
10.0
(
26 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $687
/Night
7 Nights - $4,809
House
10.0
(
13 Reviews
)
3 Bedrooms
2 Bathrooms
9 Guests
-
Private Pool -
Hot Tub
-
Parking
-
Pool
US $1,677
/Night
7 Nights - $11,740
Apartment
10.0
(
12 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
300 ft²
-
Air Conditioner
-
Internet
-
Child Friendly
-
TV
US $179
/Night
7 Nights - $1,253
Apartment
10.0
(
7 Reviews
)
3 Bedrooms
1 Bathroom
6 Guests
1500 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $322
/Night
7 Nights - $2,252
See More Winchester Vacation Rentals
Luxury Places to Stay in Winchester
Over 110+
Luxury Places to Stay in or Near Winchester
Condo
9.6
(
13 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
-
Oceanfront -
Parking
-
Ocean View -
Balcony/Terrace
US $3,231
/Night
7 Nights - $22,615
House
5 Bedrooms
4 Bathrooms
10 Guests
3229.17 ft²
-
Parking
-
View
-
Air Conditioner
-
Internet
US $2,630
/Night
7 Nights - $18,407
US $1,034
/Night
7 Nights - $7,240
House
9.8
(
7 Reviews
)
5 Bedrooms
4 Bathrooms
12 Guests
5000 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $993
/Night
7 Nights - $6,953
New
House
6 Bedrooms
3 Bathrooms
23 Guests
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Air Conditioner
US $987
/Night
7 Nights - $6,912
House
10.0
(
2 Reviews
)
5 Bedrooms
3 Bathrooms
10 Guests
3225 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $854
/Night
7 Nights - $5,975
House
10.0
(
15 Reviews
)
4 Bedrooms
3 Bathrooms
8 Guests
2000 ft²
-
Private Pool
-
Parking
-
Pool
-
Balcony/Terrace
US $786
/Night
7 Nights - $5,502
House
1 Bedroom
4 Bathrooms
12 Guests
5005.22 ft²
-
Parking
-
Air Conditioner
-
Internet
-
Child Friendly
US $765
/Night
7 Nights - $5,355
See More Winchester Luxury Vacation Rentals
Find More Winchester Villas, Resorts, & Rentals on BedroomVillas
Top-Rated Vacation Rentals with a Pool in Winchester
Over 5+
Top-Rated Vacation Rentals with a Pool in or Near Winchester
House
10.0
(
7 Reviews
)
4 Bedrooms
2 Bathrooms
6 Guests
2700 ft²
-
Private Pool
-
Parking
-
Pool
-
Balcony/Terrace
US $328
/Night
7 Nights - $2,296
US $133
/Night
7 Nights - $932
US $142
/Night
7 Nights - $995
Hotel
8.3
(
562 Reviews
)
355.21 ft²
-
Private Pool
-
Oceanfront
-
Breakfast -
Parking
US $212
/Night
7 Nights - $1,486
Hotel
8.1
(
231 Reviews
)
341.92 ft²
-
Private Pool
-
Breakfast
-
Parking
-
Pool
US $138
/Night
7 Nights - $965
Pet-Friendly Vacation Rentals in Winchester
Over 17+
Pet-Friendly Vacation Rentals in or Near Winchester
Apartment
9.4
(
23 Reviews
)
2 Bedrooms
1 Bathroom
5 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $400
/Night
7 Nights - $2,802
Apartment
9.0
(
5 Reviews
)
5 Bedrooms
2 Bathrooms
16 Guests
2400.35 ft²
-
Parking
-
Balcony/Terrace
-
View
-
Air Conditioner
US $620
/Night
7 Nights - $4,339
Apartment
8.4
(
5 Reviews
)
5 Bedrooms
2 Bathrooms
6 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $692
/Night
7 Nights - $4,845
Condo
2 Bedrooms
2 Bathrooms
6 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $368
/Night
7 Nights - $2,573
Condo
10.0
(
58 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1866 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $594
/Night
7 Nights - $4,160
House
10.0
(
9 Reviews
)
4 Bedrooms
2 Bathrooms
10 Guests
2100 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $609
/Night
7 Nights - $4,261
Apartment
3 Bedrooms
1 Bathroom
7 Guests
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $571
/Night
7 Nights - $3,996
House
4 Bedrooms
3 Bathrooms
2 Guests
2400 ft²
-
Kitchen
-
Air Conditioner
-
Internet
-
Pet Friendly
US $450
/Night
7 Nights - $3,150
See More Pet-Friendly Vacation Rentals in Winchester on PetFriendly.io
Large Vacation Homes & Villas in Winchester
Over 6+
Large Vacation Homes & Villas in or Near Winchester
House
10.0
(
1 Review
)
5 Bedrooms
2 Bathrooms
9 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $583
/Night
7 Nights - $4,083
House
9.3
(
8 Reviews
)
4 Bedrooms
2 Bathrooms
10 Guests
1496.18 ft²
-
Parking
-
View
-
Air Conditioner
-
Internet
US $580
/Night
7 Nights - $4,058
House
9.6
(
31 Reviews
)
4 Bedrooms
2 Bathrooms
10 Guests
1496 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $660
/Night
7 Nights - $4,623
House
5 Bedrooms
5 Bathrooms
6 Guests
-
Child Friendly
US $460
/Night
7 Nights - $3,220
House
4 Bedrooms
3 Bathrooms
10 Guests
-
Kitchen
-
Air Conditioner
-
Laundry -
TV
US $1,000
/Night
7 Nights - $7,000
Condo
5 Bedrooms
4 Bathrooms
10 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $443
/Night
7 Nights - $3,103
See More Family Vacation Rentals in Winchester on FVR
Wheelchair Accessible Vacation Homes in Winchester
Over 1+
Wheelchair Accessible Vacation Homes in or Near Winchester
US $155
/Night
7 Nights - $1,084
Winchester Vacation Rentals and Airbnb Places to Stay Under $200
Over 27+
Winchester Vacation Rentals and Airbnb Places to Stay Under $200
House
7.4
(
11 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
398.26 ft²
-
Private Beach -
Parking
-
Ocean View
-
View
US $161
/Night
7 Nights - $1,125
Hostel
9.0
(
2 Reviews
)
1 Bedroom
1 Bathroom
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $150
/Night
7 Nights - $1,052
Apartment
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
2 Guests
500 ft²
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $192
/Night
7 Nights - $1,346
New
House
1 Bedroom
1 Bathroom
2 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $136
/Night
7 Nights - $953
New
Apartment
10.0
(
16 Reviews
)
1 Bedroom
1 Bathroom
3 Guests
-
Kitchen
-
Air Conditioner
-
Internet
-
Child Friendly
US $196
/Night
7 Nights - $1,372
Apartment
10.0
(
12 Reviews
)
1 Bedroom
1 Bathroom
3 Guests
-
Kitchen
-
Air Conditioner
-
Internet
-
Child Friendly
US $197
/Night
7 Nights - $1,380
House
10.0
(
6 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
-
Kitchen
-
Air Conditioner
-
Internet
-
Child Friendly
US $195
/Night
7 Nights - $1,368
Apartment
10.0
(
4 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
-
Kitchen
-
Air Conditioner
-
Internet
-
Child Friendly
US $196
/Night
7 Nights - $1,372
See More Winchester Vacation Rental Deals
Instantly Bookable Vacation Homes in Winchester
Over 26+
Instantly Bookable Vacation Homes in or Near Winchester
Apartment
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
2 Guests
-
Parking
-
Balcony/Terrace
-
Air Conditioner
-
Internet
US $447
/Night
7 Nights - $3,128
House
9.8
(
12 Reviews
)
3 Bedrooms
1 Bathroom
8 Guests
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $400
/Night
7 Nights - $2,799
Apartment
9.6
(
4 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
-
Parking
-
Kitchen
-
Internet
-
Child Friendly
US $206
/Night
7 Nights - $1,439
Condo
8.8
(
11 Reviews
)
3 Bedrooms
1 Bathroom
8 Guests
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $589
/Night
7 Nights - $4,123
Apartment
7.4
(
31 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
800 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $220
/Night
7 Nights - $1,539
New
House
3 Bedrooms
1 Bathroom
6 Guests
-
Air Conditioner
-
Internet
-
Child Friendly
-
Laundry
US $653
/Night
7 Nights - $4,573
House
4 Bedrooms
2 Bathrooms
6 Guests
-
Air Conditioner
-
Internet
-
Child Friendly
-
Laundry
US $625
/Night
7 Nights - $4,378
New
House
4 Bedrooms
2 Bathrooms
-
Air Conditioner
-
Internet
-
Child Friendly
-
Bedding/Linens
US $581
/Night
7 Nights - $4,070
About Winchester Vacation Rentals
With more than 119 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 645.02 ft² on average, with prices averaging US $433 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 | 51 |
| Holiday Apartments | 50 |
| Hotels | 7 |
| Cottages | 2 |
| Hostels | 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, MA
Estiavillas offers a large selection of top attractions around Winchester. Research things to do on your vacation before you visit Winchester.
Winter Pond
Winchester Hospital
Fenway Park
Boston University
Harvard University
TD Garden
Boston Common
Faneuil Hall Marketplace
Boston Convention and Exhibition Center
New England Aquarium
Northeastern University
Boston Museum of Fine Arts
Copley Square
Harvard Square
Massachusetts General Hospital
Museum of Science
Hynes Convention Center
Massachusetts Institute of Technology
Copley Place
Boston Children's Museum
Other Places to Stay Near Winchester, MA
Winchester Vacation Rental Frequently Asked Questions
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 119 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.
