Apartment
10.0(18 Reviews)
1 Bedroom
3 Guests
Kitchen
Air Conditioner
Internet
Child Friendly
AU $277/Night
7 Nights - AU $1,938
Winchester, MA Villa Rentals
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Compare Villas, Resorts, & Rentals in Winchester
10.0
Apartment
10.0(1 Review)
1 Bedroom
2 Guests
Hot Tub
Parking
Balcony/Terrace
View
AU $423/Night
7 Nights - AU $2,963
Apartment
10.0(1 Review)
1 Bedroom
- Parking
- Kitchen
- Air Conditioner
- Internet
AU $382/Night
7 Nights - AU $2,674
Apartment
10.0(17 Reviews)
1 Bedroom
2 Guests
- Air Conditioner
- Internet
- Child Friendly
TV
AU $239/Night
7 Nights - AU $1,673
House
9.3(8 Reviews)
4 Bedrooms
10 Guests
- Parking
- Air Conditioner
- Internet
- Child Friendly
AU $821/Night
7 Nights - AU $5,750
Apartment
10.0(12 Reviews)
1 Bedroom
3 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
AU $279/Night
7 Nights - AU $1,955
Apartment
10.0(11 Reviews)
2 Bedrooms
4 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
AU $1,050/Night
7 Nights - AU $7,353
Apartment
10.0(11 Reviews)
1 Bedroom
3 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
AU $279/Night
7 Nights - AU $1,955
House
10.0(9 Reviews)
1 Bedroom
2 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
AU $385/Night
7 Nights - AU $2,692
Luxury Places to Stay in Winchester
Over 112+ Luxury Places to Stay in or Near Winchester
Condo
9.6(13 Reviews)
2 Bedrooms
6 Guests
- Parking
Ocean View- Balcony/Terrace
- View
AU $6,453/Night
7 Nights - AU $45,170
House
5 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- View
- Air Conditioner
AU $1,579/Night
7 Nights - AU $11,054
House
1 Bedroom
21 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
AU $1,474/Night
7 Nights - AU $10,317
House
10.0(3 Reviews)
4 Bedrooms
9 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $1,155/Night
7 Nights - AU $8,084
House
10.0(18 Reviews)
4 Bedrooms
8 Guests
Private Pool- Parking
Pool- Balcony/Terrace
AU $1,127/Night
7 Nights - AU $7,888
AU $1,084/Night
7 Nights - AU $7,588
House
6.0(2 Reviews)
3 Bedrooms
6 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
AU $937/Night
7 Nights - AU $6,559
House
4 Bedrooms
6 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
AU $883/Night
7 Nights - AU $6,181
Apartment
8.4(5 Reviews)
5 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $871/Night
7 Nights - AU $6,096
Top-Rated Villas with a Pool in Winchester
Over 7+ Top-Rated Private Villas with a Pool in or Near Winchester
House
10.0(7 Reviews)
4 Bedrooms
6 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
AU $465/Night
7 Nights - AU $3,253
AU $221/Night
7 Nights - AU $1,544
AU $166/Night
7 Nights - AU $1,160
AU $146/Night
7 Nights - AU $1,020
AU $159/Night
7 Nights - AU $1,115
House
10.0(19 Reviews)
3 Bedrooms
9 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
AU $2,244/Night
7 Nights - AU $15,704
AU $217/Night
7 Nights - AU $1,518
Pet-Friendly Villas in Winchester
Over 18+ Pet-Friendly Private Villas in or Near Winchester
Apartment
9.4(25 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $746/Night
7 Nights - AU $5,224
Apartment
9.0(5 Reviews)
5 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- View
- Kitchen
AU $805/Night
7 Nights - AU $5,637
Condo
6.0(1 Review)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $456/Night
7 Nights - AU $3,191
Apartment
7.0(1 Review)
2 Bedrooms
5 Guests
- Parking
- Internet
Pet Friendly- Child Friendly
AU $446/Night
7 Nights - AU $3,123
House
10.0(10 Reviews)
4 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $610/Night
7 Nights - AU $4,274
Apartment
3 Bedrooms
7 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
AU $679/Night
7 Nights - AU $4,754
Condo
10.0(62 Reviews)
3 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $862/Night
7 Nights - AU $6,031
House
10.0(30 Reviews)
4 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $715/Night
7 Nights - AU $5,005
New
Apartment
2 Bedrooms
4 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
AU $443/Night
7 Nights - AU $3,103
Large Private Villas in Winchester
Over 8+ Large Villas in or Near Winchester for Groups and Families
House
10.0(34 Reviews)
5 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $866/Night
7 Nights - AU $6,060
New
House
5 Bedrooms
12 Guests
- Air Conditioner
- Internet
- Child Friendly
Security/Safety
AU $526/Night
7 Nights - AU $3,680
House
9.6(35 Reviews)
4 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $862/Night
7 Nights - AU $6,031
House
9.6(9 Reviews)
5 Bedrooms
12 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
AU $622/Night
7 Nights - AU $4,353
House
10.0(2 Reviews)
5 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $602/Night
7 Nights - AU $4,213
Condo
5 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $628/Night
7 Nights - AU $4,397
AU $1,417/Night
7 Nights - AU $9,919
AU $652/Night
7 Nights - AU $4,563
Wheelchair Accessible Holiday Homes in Winchester
Over 1+ Wheelchair Accessible Villas and Holiday Homes in or Near Winchester
AU $187/Night
7 Nights - AU $1,309
Winchester Villas, Airbnb and Holiday Homes Under $200
Over 27+ Winchester Private Villas, Airbnb and Holiday Homes Under $200
AU $210/Night
7 Nights - AU $1,472
House
7.4(11 Reviews)
1 Bedroom
2 Guests
Private Beach- Parking
- Ocean View
- View
AU $228/Night
7 Nights - AU $1,594
House
10.0(9 Reviews)
1 Bedroom
4 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
AU $279/Night
7 Nights - AU $1,955
House
7.0(30 Reviews)
1 Bedroom
2 Guests
- Parking
- Air Conditioner
- Internet
Laundry
AU $204/Night
7 Nights - AU $1,427
Apartment
10.0(2 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $216/Night
7 Nights - AU $1,509
Apartment
10.0(1 Review)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $242/Night
7 Nights - AU $1,692
Apartment
9.6(5 Reviews)
1 Bedroom
4 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
AU $269/Night
7 Nights - AU $1,883
Apartment
1 Bedroom
1 Guest
- Balcony/Terrace
- Kitchen
- Internet
- Laundry
AU $170/Night
7 Nights - AU $1,187
Apartment
10.0(68 Reviews)
1 Bedroom
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
AU $182/Night
7 Nights - AU $1,271
Instantly Bookable Villa Rentals in Winchester
Over 30+ Instantly Bookable Private Villas in or Near Winchester
Apartment
2 Bedrooms
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
AU $613/Night
7 Nights - AU $4,291
Apartment
2 Bedrooms
4 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
AU $327/Night
7 Nights - AU $2,290
Apartment
10.0(18 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- View
- Kitchen
AU $378/Night
7 Nights - AU $2,648
Apartment
10.0(4 Reviews)
1 Bedroom
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
AU $393/Night
7 Nights - AU $2,747
Apartment
10.0(1 Review)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
AU $633/Night
7 Nights - AU $4,432
Apartment
9.6(5 Reviews)
1 Bedroom
2 Guests
- Parking
- Kitchen
- Internet
- Child Friendly
AU $202/Night
7 Nights - AU $1,413
New
House
1 Bedroom
2 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
AU $250/Night
7 Nights - AU $1,747
Apartment
9.8(9 Reviews)
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $384/Night
7 Nights - AU $2,687
House
9.6(14 Reviews)
3 Bedrooms
8 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
AU $559/Night
7 Nights - AU $3,911
Book a Last Minute Place to Stay in Winchester
About Winchester Vacation Rentals
There are more than 121 incredible getaway rentals that are available in Winchester. These choices include villas, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Relax with BedroomVillas and uncover great stays in Winchester.
BedroomVillas features numerous last-minute deals on villas, hotels, and rentals, in locations near you or across the globe. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With BedroomVillas in Winchester, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the BedroomVillas vacation rentals, resorts, and Airbnb-style properties in Winchester. Places to stay near Winchester are 577.53 ft² on average, with prices averaging AU $554 a night.
BedroomVillas helps you find the ideal holiday rental to create lifetime travel memories in Winchester. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect place to stay today.
Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods Winchester, MA
There are 7 hotels in Winchester and 103 rentals
- Prices for a holiday home in Winchester start at AU $138
- Top rated vacation home in Winchester is Garden Studio, access to I-93 to Airport, Tufts U, Hiking & Chevalier Theater.
- Most popular short term in Winchester is Best Western Plus New Englander
- Cheapest place to stay in Winchester is Spark by Hilton Woburn Boston
- Most expensive holiday rental in Winchester is Modern Two Bedroom Condo - Near Boston
Recently Booked Hotels, Resorts, or Rentals in Winchester
Frequently Asked Questions About Winchester?
What are the top hotels or resorts in Winchester?
We provide an array of great vacation destinations in Winchester. If you are looking to stay in or around the Winchester area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Winchester:
- Garden Studio, access to I-93 to Airport, Tufts U, Hiking & Chevalier Theater.
- A charming modern suburban 3 bedroom condo close to Boston
- Located north of Boston/comfort and relaxation in your home away from home
- Designer Style 3Br, King Bed, W/D,Parking,Spotless
- New 5B3B Single Family with Central AC
- Funky and cozy home ! A little bit of everything for everyone.
- Deluxe and Bright 3Br, King Bed,W/D,Parking
- Spotless and Modern Apt w/2Ba,W/D,King Bed,Parking
- Beautiful Spacious 4BRM House!
- Charming 1-bedroom well located Garden Apartment in Historic West Medford
Which hotel or resort in Winchester is best for families?
Searching for a family-friendly getaway in Winchester? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.
How many hotels, resorts, or rentals are available in Winchester?
BedroomVillas offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by BedroomVillas in 2026 is over 121 in the Winchester area, and that number rises every day. By combining listings from multiple websites and travel providers, BedroomVillas can provide you with a diverse amount of choices of the best luxury stays in Winchester.
