Vacation rentals in Winchester
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Winchester
Guests agree: these stays are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Winchester vacation rentals
Other great vacation rentals in Winchester
Home in Lynn
4.91 out of 5 average rating, 226 reviewsClean, spacious In-Law Suite -Near Everything
Jan 30 – Feb 6
Guest suite in Newton
4.97 out of 5 average rating, 556 reviewsSpacious suite with private entrance, parking spot
Aug 12 – 19
Home in Medford
4.95 out of 5 average rating, 126 reviewsSingle family home near Tufts,DT Boston,w/ parking
Sep 25 – Oct 2
Guest suite in Tyngsborough
4.98 out of 5 average rating, 215 reviewsLakefront Suite Two-Room, Comfy, Tranquil
Aug 12 – 19
Guest suite in Melrose
4.93 out of 5 average rating, 488 reviewsPrivate & Cozy Suite -near Bost-Airp-Salem-Train
Aug 16 – 23
Apartment in Woburn
5.0 out of 5 average rating, 96 reviewsCharming 1 BR private entrance apt commuters dream
Jan 11 – 18
Cottage in Winchester
4.96 out of 5 average rating, 47 reviewsThe Little House - A Historic New England cottage
Jan 9 – 16
Guest suite in Arlington
4.96 out of 5 average rating, 45 reviewsCharming 1Bd Apt. in Historic Arlington Home
Jun 16 – 23
Quick stats about vacation rentals in Winchester
Total rentals
20 properties
Popular amenities
Kitchen, Wifi, and Pool
Wifi availability
20 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Total number of reviews
940 reviews
Nightly prices starting at
€ 28 before taxes and fees
Destinations to explore
- Cape Cod Vacation rentals
- Martha's Vineyard Vacation rentals
- Cambridge Vacation rentals
- Portland Vacation rentals
- Nantucket Vacation rentals
- Salem Vacation rentals
- Philadelphia Vacation rentals
- Jersey City Vacation rentals
- New York Vacation rentals
- The Hamptons Vacation rentals
- Boston Vacation rentals
- Montreal Vacation rentals
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom