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Check prices for these dates

Next weekend
14 Rab. I - 16 Rab. I
In two weeks
21 Rab. I - 23 Rab. I
In one month
4 Rab. II - 6 Rab. II
In two months
2 Jum. I - 4 Jum. I

Compare 464 Vacation Homes in Winchester with updated reviews, rates, and availability.

Entire Home 2BR 2BTH Quite Area with parking
Fridge, microwave, oven, stovetop

Entire Home 2BR 2BTH Quite Area with parking

10.0 out of 10, Exceptional, (1)
"The Quiet Single Family House was the perfect place to stay for our group of a mom and 3 college-aged girls. We had plenty of space, the home was very clean and comfortable, and we were central to everything we wanted to do in the area. The neighborhood was peaceful and it wasn’t far to restaurants and grocery stores. The homeowner was a great source of information on things to do in the area as well as very responsive to any questions I had. I’d definitely rent from her again. We had a...
Entire Home 2BR 2BTH Quite Area with parking
Charming home with deck- walkable to transit, shops & restaurants
Fridge, microwave, oven, stovetop

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

Charming home with deck- walkable to transit, shops & restaurants
Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi
Interior

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
Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (56)
"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
Luxury Oceanfront Bayside Jewel-🔥🔥 20% off- Limited space left
Interior

Luxury Oceanfront Bayside Jewel-🔥🔥 20% off- Limited space left

10.0 out of 10, Exceptional, (67)
"My family and I had a wonderful stay at Luxury Bayside Jewel in Squantum, MA, over the holidays, and I cannot recommend this property enough. From the start, the property manager, Susan, made the experience seamless. She was incredibly responsive to all my questions before and during the trip, addressing even the smallest details—like when and where to put the trash out—with patience and care.The home itself exceeded all expectations. Thoughtful touches made us feel welcome from the moment we...
Luxury Oceanfront Bayside Jewel-🔥🔥 20% off- Limited space left
Charming 3-bedroom townhome in Marblehead 3 miles to Salem 14 miles to airport
Smart TV, books

Charming 3-bedroom townhome in Marblehead 3 miles to Salem 14 miles to airport

Charming 3-bedroom townhome in Marblehead 3 miles to Salem 14 miles to airport
Clean, Contemporary Escape | Near T
TV, offices

Clean, Contemporary Escape | Near T

Clean, Contemporary Escape | Near T
Free 2 Car Parking at this 3 bedroom apartment. Close to a park. Great location
Exterior detail

Free 2 Car Parking at this 3 bedroom apartment. Close to a park. Great location

8.8 out of 10, Excellent, (20)
"Excellent property; easy to work with owners."
The price is SAR 1,121
SAR 1,945 total
includes taxes & fees
7 Mar - 8 Mar
Free 2 Car Parking at this 3 bedroom apartment. Close to a park. Great location
Hidden Gem right in the city of Boston!
Interior

Hidden Gem right in the city of Boston!

9.8 out of 10, Exceptional, (17)
"We had a wonderful stay. The apartment was exactly as advertised. It’s very clean and in a cute borough with some great restaurants and shops and any other convenience you might need. The apartment has a large kitchen that’s great for cooking your own meals if you wish to do so. Check in was completely seamless even though we were arriving late at night. "
The price is SAR 488
SAR 1,479 total
includes taxes & fees
24 Mar - 25 Mar
Hidden Gem right in the city of Boston!
Boston's Best Vacation Home
Exterior

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
Family-Friendly Rose Cottage | Near Encore | 4 Beds 3 Baths
Living area

Family-Friendly Rose Cottage | Near Encore | 4 Beds 3 Baths

10.0 out of 10, Exceptional, (12)
"Place was great and host linda was very accommodating "
Family-Friendly Rose Cottage | Near Encore | 4 Beds 3 Baths
Bright Boston House | near T
Fridge, microwave, oven, stovetop

Bright Boston House | near T

Bright Boston House | near T
Cozy 3bdr Free parking/Wifi, 5 min to Encore Close to Boston,Cambridge ,Salem
Aerial view

Cozy 3bdr Free parking/Wifi, 5 min to Encore Close to Boston,Cambridge ,Salem

9.2 out of 10, Wonderful, (24)
"Everything was as expected. Convenient location. Would recommend."
Cozy 3bdr Free parking/Wifi, 5 min to Encore Close to Boston,Cambridge ,Salem
Beautiful coastal 5-BR in Swampscott - 5 mins to beach, Wifi, gas fireplace
Miscellaneous

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
Cozy three-bedroom home close to Boston
3 bedrooms, desk, iron/ironing board, free WiFi

Cozy three-bedroom home close to Boston

10.0 out of 10, Exceptional, (27)
"Thank you for sharing your wonderful house to us. "
The price is SAR 881
SAR 1,881 total
includes taxes & fees
19 Mar - 20 Mar
Cozy three-bedroom home close to Boston
Home Away From Home in Lowell
Outdoor dining

Home Away From Home in Lowell

10.0 out of 10, Exceptional, (7)
"Very nice house with everything you would want!"
Home Away From Home in Lowell
CityScape: Sleek Urban Oasis; Parking, Near: Boston, Casino, Airport, Parks, Hospitals, Buses
Beach

CityScape: Sleek Urban Oasis; Parking, Near: Boston, Casino, Airport, Parks, Hospitals, Buses

2.0 star property
9.6 out of 10, Exceptional, (13)
"Beautiful home, spacious, clean, warm, and cozy. Enough space for a family of 5. The neighborhood was easy to find and navigate. The mattresses were not as supportive as we’re used to but we didn’t go to Boston/Chelsea to sleep. The shower was excellent. The owner lives close by which came in handy when the smoke detectors went off on our first night and we couldn’t figure out why. He was prompt in making sure we were safe and the house wasn’t burning and then proceeded to take care of the...
CityScape: Sleek Urban Oasis; Parking, Near: Boston, Casino, Airport, Parks, Hospitals, Buses
2BR with a king, queen-beds sofa bed 65’’TV free parking close to everything
Exterior detail

2BR with a king, queen-beds sofa bed 65’’TV free parking close to everything

9.0 out of 10, Wonderful, (25)
"Great stay, communication was amazing "
The price is SAR 765
SAR 1,638 total
includes taxes & fees
19 Mar - 20 Mar
2BR with a king, queen-beds sofa bed 65’’TV free parking close to everything
Beautiful renovated 3 bedroom apt near Boston.
Fridge, microwave, oven, stovetop

Beautiful renovated 3 bedroom apt near Boston.

9.8 out of 10, Exceptional, (73)
"We’re a band from Jersey. We play at Ned Devines and The Harp in Boston a few times a year. As a band, budgeting is crucial. Housing 4 people can be super expensive. This property has a great price point allowing some money left over in the budget to buy groceries at a close by grocery store. We were able to check in, go to the gym together, grocery shop, and relax, all before heading to the venue to check in. Finding a place with a clean safe neighborhood for parking our vehicles and feeling...
Beautiful renovated 3 bedroom apt near Boston.
Funky and cozy home ! A little bit of everything for everyone.
Fridge, microwave, oven, stovetop

Funky and cozy home ! A little bit of everything for everyone.

2.0 star property
10.0 out of 10, Exceptional, (7)
"Great house for me and my wife and two adult daughters, plus our two dogs.Everything about the house is wonderful and adaptable to groups of various sizes. The house is big enough that everyone can have their own space for reading, working etc. There is a great family room as you enter, as well as a sun room in front and very nice dining room and kitchen. Comfortable beds and very nice bathrooms. Dogs loved the easy access to the spacious fenced-in yard. Owner lives onsite and responded...
The price is SAR 938
SAR 1,785 total
includes taxes & fees
9 Mar - 10 Mar
Funky and cozy home ! A little bit of everything for everyone.
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
Interior

Sonder 907 Main

4.0 star property
8.2 out of 10, Very Good, (444)
"Know that this is a typical small Boston room. There is no dresser. The microwave is in the hall and there is no parking. However, the shower and the toiletries provided are great! Overall, if you can get past the size of the room this hotel is really nice. Make sure to get coffee and pastries from the French bakery next door. "
The price is SAR 657
SAR 762 total
includes taxes & fees
9 Mar - 10 Mar
Sonder 907 Main
No. 284 powered by Sonder
Exterior

No. 284 powered by Sonder

4.0 star property
9.4 out of 10, Exceptional, (874)
"Very quaint, clean space with amazing access to the Boston area. Right between Newbury and Comm Ave, with lots to eat and enjoy."
The price is SAR 680
SAR 803 total
includes taxes & fees
9 Mar - 10 Mar
No. 284 powered by Sonder
Temple Place Suites
Deluxe Studio | Desk, iron/ironing board, free WiFi, bed sheets

Temple Place Suites

2.5 star property
6.8 out of 10, (186)
" alue"
The price is SAR 402
SAR 668 total
includes taxes & fees
19 Mar - 20 Mar
Temple Place Suites
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.