Winchester Vacation Rentals
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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
8.6 out of 10, Excellent, (19 reviews)
"Great place, friendly check-in"
Anonymous traveller
The price is CA $129
CA $500 total
includes taxes & fees
Nov 10 - Nov 11
2. Tufts 4BD/2BA - 5.MIN to Harvard&Boston / Free Parking / Walk to Subway
Tufts 4BD/2BA - 5.MIN to Harvard&Boston / Free Parking / Walk to SubwayWest Somerville
8.2 out of 10, Very good, (18 reviews)
"Very clean home and easy onsite parking. Good location as well!"
Katie D.
The price is CA $251
CA $596 total
includes taxes & fees
Nov 18 - Nov 19
3. Enchanting Hidden Door Escape
Enchanting Hidden Door EscapeStoneham
9.6 out of 10, Exceptional, (37 reviews)
"Property was very nice! Updated and clean!"
Aimee M.
The price is CA $351
CA $860 total
includes taxes & fees
Nov 15 - Nov 16
4. Spacious & Convenient 1BR unit-20min to Boston
Spacious & Convenient 1BR unit-20min to BostonMelrose
9.6 out of 10, Exceptional, (20 reviews)
"very pleased with our stay! "
Patrick G.
The price is CA $253
CA $521 total
includes taxes & fees
Nov 12 - Nov 13
5. Recently Renovated Extremely Spacious Home For You
Recently Renovated Extremely Spacious Home For YouMedford
7.4 out of 10, Good, (6 reviews)
"The property was exactly as advertised. Spacious bedrooms, a well-stocked kitchen, and plenty of space for 8 people. There is a Target only 3 minutes away, and loads of small restaurants within walking distance. My family and I were very pleased with the house. Thank you for the positive experience!"
Hak-Jai K.
The price is CA $212
CA $591 total
includes taxes & fees
Nov 10 - Nov 11
6. 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, (157 reviews)
"We enjoyed our stay! Great location, easy parking. Wonderful communication from host. Would stay again!"
Martha W.
The price is CA $336
CA $780 total
includes taxes & fees
Nov 17 - Nov 18
7. PEACE IN THE CITY - Humble Luxury minutes from Boston, Beach & Casino
PEACE IN THE CITY - Humble Luxury minutes from Boston, Beach & CasinoEverett
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful and clean. Very friendly and helpful host. If ever in the area would definitely choose this lovely home first!"
Dawn B.
The price is CA $227
CA $417 total
includes taxes & fees
Nov 11 - Nov 12
8. Funky and cozy home ! A little bit of everything for everyone.
Funky and cozy home ! A little bit of everything for everyone.Arlington
10.0 out of 10, Exceptional, (30 reviews)
"Awesome, clean, lots of room, great amenities."
Craig R.
The price is CA $468
CA $841 total
includes taxes & fees
Nov 16 - Nov 17
9. 15 Min to Boston, Spacious 5BR Retreat on Road with Office Space & Comfortable Beds
15 Min to Boston, Spacious 5BR Retreat on Road with Office Space & Comfortable BedsStoneham
10.0 out of 10, Exceptional, (4 reviews)
"This house was exactly as described and perfect for our family trip."
Deb W.
The price is CA $461
CA $1,163 total
includes taxes & fees
Nov 30 - Dec 1
10. Cozy Davis SQ 4BDs/Free Parking/7 Min to Harvard & MIT/5 Min Walk-Train Station
Cozy Davis SQ 4BDs/Free Parking/7 Min to Harvard & MIT/5 Min Walk-Train StationDavis Square
6.0 out of 10, (5 reviews)
"Great location. Host was communicative and easy to connect with. "
Joe C.
The price is CA $243
CA $518 total
includes taxes & fees
Nov 16 - Nov 17
11. Beautiful condo next to commuter rail into Boston
Beautiful condo next to commuter rail into BostonWakefield
9.6 out of 10, Exceptional, (31 reviews)
"The home was in a great neighborhood. The home is also super clean and hosts were responsive and helpful. "
Melissa A.
The price is CA $303
CA $719 total
includes taxes & fees
Nov 11 - Nov 12
12. Eagles Landing - Logan Airport
Eagles Landing - Logan AirportEast Boston
10.0 out of 10, Exceptional, (1 review)
The price is CA $150
CA $280 total
includes taxes & fees
Nov 12 - Nov 13
13. LUXE 4BDR/2BA Near Boston- T-Station & Encore Casino
LUXE 4BDR/2BA Near Boston- T-Station & Encore CasinoEast Somerville
9.6 out of 10, Exceptional, (8 reviews)
"Very sweet place to stay. Located in a very nice area. Close to the "T" and very walkable "
Tobakeion B.
The price is CA $199
CA $586 total
includes taxes & fees
Nov 17 - Nov 18
14. SkyDeck Stylish Stay
SkyDeck Stylish StayWinter Hill
The price is CA $473
CA $1,076 total
includes taxes & fees
Nov 10 - Nov 11
15. Cozy 3bdr Free parking/Wifi, 5 min to Encore Close to Boston,Cambridge ,Salem
Cozy 3bdr Free parking/Wifi, 5 min to Encore Close to Boston,Cambridge ,SalemEverett
8.8 out of 10, Excellent, (50 reviews)
"This is our second time staying here. We find it so nice and great for traveling to Boston! The host is great and responsive."
Shannon K.
The price is CA $248
CA $585 total
includes taxes & fees
Nov 10 - Nov 11
16. Harvard Charm / Near Boston + New build
Harvard Charm / Near Boston + New buildWard Two
The price is CA $215
CA $620 total
includes taxes & fees
Nov 10 - Nov 11
17. The Everett House - Five Bedroom House, Sleeps 11
The Everett House - Five Bedroom House, Sleeps 11Everett
10.0 out of 10, Exceptional, (3 reviews)
"We stayed here for my brother’s MIT graduation, and I cannot say enough good things about this stunning property. Finding a home that comfortably fits the whole family can be a challenge, but this place was absolutely perfect. The house is gorgeous, incredibly spacious, and felt like a true home away from home. Being so close to Cambridge made our commute to the commencement events stress-free. If you’re looking for a beautiful, high-end spot for a family gathering, look no further. Five stars...
Meshullam
The price is CA $687
CA $990 total
includes taxes & fees
Nov 30 - Dec 1
18. Home for Families | Sleeps 11 | 5 min Downtown
Home for Families | Sleeps 11 | 5 min DowntownChelsea
10.0 out of 10, Exceptional, (1 review)
The price is CA $427
CA $466 total
includes taxes & fees
Nov 11 - Nov 12
19. Modern 2BR Getaway Near Revere Beach
Modern 2BR Getaway Near Revere BeachRevere
10.0 out of 10, Exceptional, (1 review)
"Great home! Quiet neighborhood, great home, and excellent communication from the host. We had a great stay."
Steve S.
The price is CA $311
CA $521 total
includes taxes & fees
Nov 10 - Nov 11
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.
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Top Winchester Hotel Reviews
The Godfrey Hotel Boston
10/10 Excellent
Find out more about Winchester
Winchester Vacation Homes information
Number of reviews | 372 |
|---|---|
Accommodation | 530 Vacation Homes |
Lowest Price | CA $280 |
Highest Price | CA $1,163 |
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