Search Vacation Homes in Winchester
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Winchester vacation homes
1. Cozy 4BR Home by Tufts w/ Subway Access to Downtown, MIT, Harvard + Free Parking
Cozy 4BR Home by Tufts w/ Subway Access to Downtown, MIT, Harvard + Free ParkingSouth Medford
9.6 out of 10, Exceptional, (9 reviews)
"Clean rooms and comfortable beds "
camilo r.
The price is AED 413
AED 1,466 total
includes taxes & fees
23 Aug - 24 Aug
2. 5-bedroom house. Close to airport, bus & train. 10 min from Boston. Sleeps 10.
5-bedroom house. Close to airport, bus & train. 10 min from Boston. Sleeps 10.Melrose
10.0 out of 10, Exceptional, (147 reviews)
"Everything was outstanding and we had a really great time! Would highly recommend! Greg was a really great host as well."
Ashley K.
The price is AED 1,276
AED 2,542 total
includes taxes & fees
16 Aug - 17 Aug
3. Spacious & Convenient 1BR unit-20min to Boston
Spacious & Convenient 1BR unit-20min to BostonMelrose
9.8 out of 10, Exceptional, (16 reviews)
"very pleased with our stay! "
Patrick G.
The price is AED 658
AED 1,428 total
includes taxes & fees
10 Aug - 11 Aug
4. 2 bedroom's 1 bathroom 10 min-Airport/Downtown Boston 7 min-Encore Casino
2 bedroom's 1 bathroom 10 min-Airport/Downtown Boston 7 min-Encore CasinoEverett
10.0 out of 10, Exceptional, (12 reviews)
"Great neighborhood! House is beautiful and alot bigger then expected! If we ever get back to the area, this would be my first pick to stay. "
Danielle s.
The price is AED 529
AED 1,239 total
includes taxes & fees
11 Aug - 12 Aug
5. Boston 2Bd Kg-Qn Bds entire unshared space near Harvard, MIT Subway w/parking
Boston 2Bd Kg-Qn Bds entire unshared space near Harvard, MIT Subway w/parkingWard Two
9.8 out of 10, Exceptional, (16 reviews)
"We were in Boston to attend graduation. The location is perfect, in a quiet neighborhood yet still central and close to everything. T was readily accessible and just a few minutes walking. Onsite parking space was convenient. Check out was a breeze, hassle free, nothing extra for us to take care of. Great stay. "
Elaine W.
The price is AED 729
AED 1,594 total
includes taxes & fees
9 Aug - 10 Aug
6. Cozy Large House close to TUFTS/Harvard/MIT 4BR
Cozy Large House close to TUFTS/Harvard/MIT 4BRSouth Medford
9.8 out of 10, Exceptional, (11 reviews)
"Good size. Good communication from host. Safe, quiet neighborhood."
Keith
The price is AED 885
AED 2,179 total
includes taxes & fees
10 Aug - 11 Aug
7. Cozy House close to TUFTS, Harvard, MIT 3BR
Cozy House close to TUFTS, Harvard, MIT 3BRSouth Medford
9.6 out of 10, Exceptional, (15 reviews)
"Great stay and as advertised. Beds were very comfortable, unit was very clean, and ideal location for visiting Medford area!"
Michael C.
The price is AED 925
AED 2,189 total
includes taxes & fees
11 Aug - 12 Aug
8. Enchanting Hidden Door Escape
Enchanting Hidden Door EscapeStoneham
9.6 out of 10, Exceptional, (33 reviews)
"The house was the perfect size for our family- 5 adults 4 kids. The house was super clean, had all the supplies we needed, and was conveniently located to shopping, highway, and a short drive to the metro. The communication with the host was speedy and all my questions were answered ahead of time. Check in and check out was super easy as well. Would definitely stay again. "
Jess C.
The price is AED 1,184
AED 2,606 total
includes taxes & fees
16 Aug - 17 Aug
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Find vacation rentals that suit your style
Aparthotels
Apartments
Save an average of 15% on thousands of hotels when you're signed in
Top Winchester Hotel Reviews
Copley Square Hotel, a FOUND Hotel
10/10 Excellent
Explore a world of travel with Expedia
- Fairmont Hotels in Winchester
- Villas in Malden
- Inns in Medford
- Villas in Melrose
- Historic Hotels in Arlington
- Hyatt Hotels in Medford
- Motels in Medford
- Accor Hotels in Melrose
- Extended Stay America Hotels in Winchester
- Red Roof Inn Hotels in Arlington
- Morgans Hotel Group in Melrose
- Hostels in Medford
- Condo Rentals in Belmont
- Oakwood Hotels in Winchester
- Hyattvacations Supechain Hotels in Woburn
- Apartments in Medford
- Hostels in Melrose
- Inns in Woburn
- Red Roof Inn Hotels in Woburn
- Fairmont Hotels in Arlington
- Marriott Hotels & Resorts in Medford
- Sonesta Hotel in West Medford
- 5 Star Hotels in Medford
- Morgans Hotel Group in Arlington
- 4 Star Hotels in Medford
- 3 Star Hotels in Woburn
- Woburn Hotels
- Hostelling International Hotels in Arlington
- Langham Hotels in Melrose
- Loews Hotels in Winchester
- Vacation Homes in Alewife Station
- Hostels in Woburn
- Langham Hotels in Woburn
- B&B in Winchester Wedgemere Station
- Sonesta Hotel in Arlington
- Guest Houses in Davis Station
- Kimpton Hotels in Arlington
- Four Seasons Hotels in West Medford
- Concorde Hotels in Arlington
- B&B in Medford
- Four Seasons Hotels in Winchester
- Farmstay in Melrose Highlands Station
- Cottages in Stoneham
- 3 Star Hotels in Arlington
- Marriott Hotels & Resorts in Melrose
- Apartments in Melrose
- Gemstone Resorts in Melrose
- Marriott Hotels & Resorts in West Medford
- Hilton Hotels in Stoneham
- Guest Houses in Winchester Wedgemere Station
- Guest Houses in Melrose
- 4 Star Hotels in West Medford
- Marriott Hotels & Resorts in Arlington
- Cottages in Wakefield Greenwood Station
- Stoneham Hotels
- Four Seasons Hotels in Woburn
- Villas in Woburn
- Hotels near Oak Grove Station
- Hostelling International Hotels in Stoneham
- Red Roof Inn Hotels in Medford
- Apartments in Melrose Wyoming Hill Station
- Mandarin Oriental Hotel Group in Woburn
- Aparthotels in Arlington
- Cottages in Winchester Wedgemere Station
- Preferred Hotels in Melrose
- Red Roof Inn Hotels in Stoneham
- Houseboats in Winchester
- Kimpton Hotels in Stoneham
- Hotels near Winchester Wedgemere Station
- 5 Star Hotels in Stoneham
- 4 Star Hotels in Woburn
- Club Quarters Hotels in West Medford
- Hyatt Hotels in Woburn
- 5 Star Hotels in Woburn
- Preferred Hotels in West Medford
- La Quinta Inn & Suites Hotels in West Medford
- B&B in Melrose
- Independent Hotels in West Medford
- Vacation Homes in Melrose Highlands Station
- Oakwood Hotels in Medford
- Hyattvacations Supechain Hotels in Medford
- Aramark Parks & Destinations Hotels in West Medford
- Club Quarters Hotels in Stoneham
- Extended Stay America Hotels in Woburn
- Guest Houses in Malden
- Extended Stay America Hotels in Arlington
- Taj Hotels in Winchester
- La Quinta Inn & Suites Hotels in Woburn
- Pyramid Hotels in Stoneham
- Premier Inn Hotels in Stoneham
- Hostels in Alewife Station
- Gemstone Resorts in Arlington
- Condo Rentals in Malden
- Citizenm Hotels in Medford
- Hilton Hotels in West Medford
- 2 Star Hotels in Woburn
- Accor Hotels in Stoneham