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Check prices for these dates

Next weekend
14 Feb - 16 Feb
In two weeks
21 Feb - 23 Feb
In one month
7 Mar - 9 Mar
In two months
4 Apr - 6 Apr

Compare 468 Vacation Homes in Winchester with updated reviews, rates, and availability.

Modern & Walkable to city sights. A 4-bedroom house in wonderful Boston
Private kitchen

Modern & Walkable to city sights. A 4-bedroom house in wonderful Boston

Modern & Walkable to city sights. A 4-bedroom house in wonderful Boston
Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC
Exterior

Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC

9.6 out of 10, Exceptional, (110)
"Our third stay at 14 Hodges. We were so pleased with the upgrades. The new beds/bedding were amazing and the new thermostat was user friendly. We managed to cook quite a bit while also eating out at our favorite vegan spots in Salem and Beverly. We headed to Boston via train for the Titanic exhibit and headed to Portland Maine and the lit up for the Holidays Nubble Light House. It was great to visit the PEM once again for some great exhibits and all the local stores. It was great to be "home." "
Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC
Charming home with deck- walkable to transit, shops & restaurants

Charming home with deck- walkable to transit, shops & restaurants

Charming home with deck- walkable to transit, shops & restaurants
Beautiful coastal 5-BR in Swampscott - 5 mins to beach, Wifi, gas fireplace
Living room

Beautiful coastal 5-BR in Swampscott - 5 mins to beach, Wifi, gas fireplace

Beautiful coastal 5-BR in Swampscott - 5 mins to beach, Wifi, gas fireplace
OLD TOWN CHARM. Sleeps 4- 2 bedrooms - 2.5 baths
Exterior

OLD TOWN CHARM. Sleeps 4- 2 bedrooms - 2.5 baths

9.6 out of 10, Exceptional, (9)
"Loved this old historic home and the town. Had everything we needed to make our stay comfortable. Would love to come back again! Everything was walkable. Charming town. Gorgeous ocean all around. In love!"
OLD TOWN CHARM. Sleeps 4- 2 bedrooms - 2.5 baths
Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!
Private kitchen

Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!

9.6 out of 10, Exceptional, (72)
"Clean and convenient. Loud neighbors"
Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!
Villa in Boston 6BR 5.5 Bath-IGLOO, Arcade, Parking,Game Room,EV
Property grounds

Villa in Boston 6BR 5.5 Bath-IGLOO, Arcade, Parking,Game Room,EV

10.0 out of 10, Exceptional, (2)
"We had an incredible experience staying at this property! The house was absolutely beautiful and exceeded our expectations. It was clean, well-maintained, and had everything we needed for a comfortable and relaxing stay. My family loved it so much, and we're already planning to come back in the future. Thank you to our wonderful host for making this stay so memorable!"
Villa in Boston 6BR 5.5 Bath-IGLOO, Arcade, Parking,Game Room,EV
Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
Bathroom

Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston

10.0 out of 10, Exceptional, (55)
"Really enjoyed the house. Great location, easy checking in. They even had a decorated Christmas tree for us."
Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi
Building entrance

Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi

9.8 out of 10, Exceptional, (155)
"Nice neighborhood. My only concern was there are a lot of stairs.Great location close to everything, Good restaurants close by. Had a wonderful time. "
Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi
Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino
Boston Harbor and Downtown Skyline Views

Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino

9.4 out of 10, Exceptional, (79)
"House was well stocked, clean and accurately advertised. Would stay here again!"
The price is AED 918
AED 2,014 total
includes taxes & fees
11 Feb - 12 Feb
Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino
Remodeled Townhouse close to Boston
Living area

Remodeled Townhouse close to Boston

9.8 out of 10, Exceptional, (24)
"At this price point it was exactly as we expected, and we were very happy with the place and it met all our needs."
Remodeled Townhouse close to Boston
Norwood Luxe Suite- Pet friendly & Commuter friendly
Dining area seats 8

Norwood Luxe Suite- Pet friendly & Commuter friendly

10.0 out of 10, Exceptional, (8)
"Our crew have been up several times in the area for work and really enjoyed staying here. The house is lovely and is always clean and welcoming when they arrive for their stay. Susan is an excellent communicator and a wonderful host!"
Norwood Luxe Suite- Pet friendly & Commuter friendly
Beach-view home with beach access, deck, grill, washer/dryer, 2 kayaks, & AC

Beach-view home with beach access, deck, grill, washer/dryer, 2 kayaks, & AC

10.0 out of 10, Exceptional, (3)
"This place was so peaceful and relaxing "
Beach-view home with beach access, deck, grill, washer/dryer, 2 kayaks, & AC
Boston's Best Vacation Home
Outdoor View

Boston's Best Vacation Home

9.8 out of 10, Exceptional, (44)
"We had a pleasant stay. The house is cozy, clean and comfortable. It is in a convenient location with several restaurants in walking distance as well as a supermarket. The neighborhood is quiet with little traffic coming through. Victor the host was responsive and answered any questions we had. Would recommend without hesitation."
Boston's Best Vacation Home
Centrally located in the heart of Boston near T
Living area

Centrally located in the heart of Boston near T

8.8 out of 10, Excellent, (16)
"The apartment was beautiful and super clean. My bed was comfortable. I thoroughly enjoyed my stay. The parking is a little nerve-racking but it all worked out. I would definitely recommend this for anyone who’s looking to stay in the Boston area."
The price is AED 643
AED 1,634 total
includes taxes & fees
9 Feb - 10 Feb
Centrally located in the heart of Boston near T
5-bedroom house. Close to airport, bus & train. 10 min from Boston. Sleeps 10.
Entrance

5-bedroom house. Close to airport, bus & train. 10 min from Boston. Sleeps 10.

10.0 out of 10, Exceptional, (125)
"This house is perfect in every way. Plenty of space, great location and tons of charm. Will definitely stay again! "
5-bedroom house. Close to airport, bus & train. 10 min from Boston. Sleeps 10.
Rare Find in Boston's Hippest Neighborhood
Your exclusive patio and garden off the deck outside the kitchen.

Rare Find in Boston's Hippest Neighborhood

10.0 out of 10, Exceptional, (89)
"Margaret was a wonderful host and communicated extremely promptly. Location was great, in close walking distance to public transportation and J.P. Downtown. We enjoyed making a cozy fire in the wood stove on a cool November evening. All in all a comfortable weekend with the family."
Rare Find in Boston's Hippest Neighborhood
Peaceful 2Br House in Cambridge
Exterior

Peaceful 2Br House in Cambridge

2.0 star property
6.0 out of 10, (5)
"A marvelous place. Parking spot was appeciated!"
Peaceful 2Br House in Cambridge
Entire 4BR 2 Bath Home l Minutes to Downtown Salem
When you arrive to Salem look for the pink home with a gravel driveway!

Entire 4BR 2 Bath Home l Minutes to Downtown Salem

2.0 star property
10.0 out of 10, Exceptional, (2)
"A lovely little antique house with more space than you would expect- beautiful old floor boards, nice linens, plenty of coffee options and a well stocked kitchen. I would certainly stay again. "
Entire 4BR 2 Bath Home l Minutes to Downtown Salem
Heart of Southie - Hot Tub + Walk to Top Bars
Main Living Area

Heart of Southie - Hot Tub + Walk to Top Bars

10.0 out of 10, Exceptional, (11)
"The property was great to visit with friends. Close to pickleball, candlepin bowling, and great food! The kitchen is on the bottom floor of where you entertain. There is a hot tub that we did not use because it was cold in January!"
Heart of Southie - Hot Tub + Walk to Top Bars
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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Other property types in Winchester

Sonder 907 Main
Room

Sonder 907 Main

4.0 star property
8.2 out of 10, Very Good, (429)
"Came for a business trip. My first sonder. Great for just the parts i needed and not over the top. "
The price is AED 472
AED 548 total
includes taxes & fees
12 Feb - 13 Feb
Sonder 907 Main
No. 284 powered by Sonder
Room

No. 284 powered by Sonder

4.0 star property
9.4 out of 10, Exceptional, (863)
"The property was easy to get in and out of and close to many shops and restaurants"
The price is AED 566
AED 667 total
includes taxes & fees
10 Feb - 11 Feb
No. 284 powered by Sonder
Global Luxury Suites Downtown Boston
Living room

Global Luxury Suites Downtown Boston

4.0 star property
8.0 out of 10, Very Good, (526)
"There was not any parking onsite-I had to ask a random person where to park because no one answered the phone when I called multiple times. there wasn’t anyone at the front door. I wasn’t able to get in the building. I had to wait outside in the cold until someone who was leaving the building let me in. The suite was really nice and comfortable. Make sure you bring laundry detergent, extra paper towels, and dishwasher detergent and extra garbage bags. The location is perfect. Very easy to get...
The price is AED 363
AED 863 total
includes taxes & fees
12 Feb - 13 Feb
Global Luxury Suites Downtown Boston
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.