Search Vacation Homes in Winchester

  • Plan, book, stay with confidence
    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 412 Vacation Homes in Winchester with updated reviews, rates, and availability.

Gorgeous Beacon Hills Studio next to State house
Room

Gorgeous Beacon Hills Studio next to State house

10.0 out of 10, Exceptional, (14)
"Enjoyed our stay here. Room very clean and accommodations good. Nice area. Near State House and Park Street subway. "
The price is AED 547
AED 937 total
includes taxes & fees
1 Dec - 2 Dec
Gorgeous Beacon Hills Studio next to State house
Charming 2-bedroom house in superb Boston with WiFi
Room

Charming 2-bedroom house in superb Boston with WiFi

8.0 out of 10, Very Good, (1)
"I had booked this same accommodation on another site who CANCELLED me. I immediately frantically contacted Beatrice who calmed me down assuring me I would have a reservation. She and I worked together and figured it out! I have already booked this accommodation for July 2025! There’s a great place to eat breakfast and any other time. Joe’s… about a 4 minute walk!!"
The price is AED 635
AED 1,077 total
includes taxes & fees
26 Nov - 27 Nov
Charming 2-bedroom house in superb Boston with 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

9.6 out of 10, Exceptional, (75)
"We loved this location for our girls trip! The owner was excellent in responding to all our questions and needs. The views from the home are beautiful. If noise bothers you, this is very close to the airport and there is some type of industrial operation on the river. So you do hear airplanes all night as well as very loud metal banging from the river that starts early in the morning. I only mention this as an FYI! It did not lower the rating for us personally! "
The price is AED 1,469
AED 2,720 total
includes taxes & fees
1 Dec - 2 Dec
Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino
CityScape: Sleek Urban Oasis; Parking, Near: Boston, Casino, Airport, Parks, Hospitals, Buses

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

2.0 star property
9.6 out of 10, Exceptional, (12)
"The Chelsea house is a great place to stay. It is a great location to visit Boston. There are some local eateries within walking distance plus a Dunkin Donuts. The house was very clean and had all the amenities you’d need. The bedrooms are on the second and third floors. I would definitely stay here again. "
The price is AED 606
AED 1,887 total
includes taxes & fees
2 Dec - 3 Dec
CityScape: Sleek Urban Oasis; Parking, Near: Boston, Casino, Airport, Parks, Hospitals, Buses
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
Beautiful, Cozy Ultra Convenient Salem Home
Room

Beautiful, Cozy Ultra Convenient Salem Home

8.2 out of 10, Very Good, (32)
"Overall the house was fine. The location was perfect (close to Salem, but the neighborhood was quiet) and the beds were super comfortable. My recommendations would be to have a tv in the first floor living area and tvs in the bedrooms as well. Also some kind of curtain or frosted glass in the upstairs bathroom for privacy, since it looks right out onto the Salem State fields."
The price is AED 599
AED 1,116 total
includes taxes & fees
26 Nov - 27 Nov
Beautiful, Cozy Ultra Convenient Salem Home
Leslie's Retreat: Spacious home ideally located to everything
Leslie's Retreat a great place to meet!

Leslie's Retreat: Spacious home ideally located to everything

10.0 out of 10, Exceptional, (218)
"This house was perfect for us. Plenty of room, comfortable beds, quiet neighborhood, and an easy walk to downtown. The host was very responsive and friendly. I would highly recommend starting at this property. "
Leslie's Retreat: Spacious home ideally located to everything
Boston's Best Vacation Home
Outdoor View

Boston's Best Vacation Home

9.8 out of 10, Exceptional, (43)
"I stayed here with family members. We thought the property was very lovely and in a pleasant neighborhood. Everything we could need was in the house. We especially appreciated the toiletries and the Nespresso provided. Kitchen was fully functional. The property was very clean and the bedrooms and living spaces were nicely decorated. It felt more personable and comfortable than staying in a hotel. It was truly a nice getaway for us who were in the area to explore Boston!"
Boston's Best Vacation Home
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, (106)
"The property is comfortable and clean. The location is perfect, right at the harbor with an excellent cafe right across the street. I have stayed at a few VRBO properties and never had plenty of toilet paper, soap, shampoo, conditioner, trash bags, etc provided. That was a fantastic surprise. If a may make one tiny suggestion, a row of coat hooks next to the front door would be a cheap, but much appreciated addition. Again, this property is wonderful and if I make my way back to Salem I will...
Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC
Newly renovated home, top of the line appliances.
Kitchen

Newly renovated home, top of the line appliances.

9.8 out of 10, Exceptional, (109)
"The house was beautiful, clean, spacious with everything we needed. Loved it."
Newly renovated home, top of the line appliances.
Dog-friendly home with a partial river view & deck - steps from park & beach

Dog-friendly home with a partial river view & deck - steps from park & beach

8.8 out of 10, Excellent, (12)
"The location was perfect! A 4 minute drive to Salem and was xlose wnto the interstate but yet far enough away that you didn't hear the traffic. The house was across the street feom a park and had eaa path to walk down to thw shoreline."
Dog-friendly home with a partial river view & deck - steps from park & beach
West End Deluxe Suite-Thanksgiving DEAL 🔥SAVE up to 20% Long term stays welcome!
Interior

West End Deluxe Suite-Thanksgiving DEAL 🔥SAVE up to 20% Long term stays welcome!

9.8 out of 10, Exceptional, (49)
"Loved this house! Everything was perfect, easy to communicate with the owner and so clean and lovely!"
West End Deluxe Suite-Thanksgiving DEAL 🔥SAVE up to 20% Long term stays welcome!
Like a 5 Star hotel
Master Bedroom

Like a 5 Star hotel

10.0 out of 10, Exceptional, (9)
"The post does the property justice it was exactly what we expected. "
The price is AED 1,286
AED 2,156 total
includes taxes & fees
30 Nov - 1 Dec
Like a 5 Star hotel
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
6 bedroom house in a quiet and convenient neighborhood
Exterior

6 bedroom house in a quiet and convenient neighborhood

6.8 out of 10, (3)
"The good, Large House, lots of bedrooms. Felt very safe, nice Alarm system. And the Piano was very fun for a singing and having fun. Reconstruction in process. The bad, the beds, not good, the house is falling apart, scary stairs, the bath rooms are tiny and do not offer shampoo, conditioner, and conditioner. Could not find bath towels. The ugly - mouse droppings all over the kitchen. Mouse found in one bedroom, captured mouse and took outside. Let host know that there was a mouse and mice...
6 bedroom house in a quiet and convenient neighborhood
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, (1)
"My family & I booked a trip to Salem and we desired to find a cute home that would accommodate 7 of us that was within walking distance of downtown Salem and we found just that in this home! The host was a great communicator & really was fantastic at making our stay welcoming and pleasant. We were able to walk to all the tourist sites and restaurants within a short amount of time. Would recommend staying here 10/10. "
The price is AED 598
AED 1,702 total
includes taxes & fees
2 Dec - 3 Dec
Entire 4BR 2 Bath Home l Minutes to Downtown Salem
*Spooky 2Br Halloween Sleeps 6 |DowntownSalem
Step into a space where every corner tells a story! My home is filled with art that captures the spirit of our local artists and adds a warm, unique touch to your stay.

*Spooky 2Br Halloween Sleeps 6 |DowntownSalem

9.6 out of 10, Exceptional, (34)
"Cute decorations. In a"
The price is AED 771
AED 1,513 total
includes taxes & fees
30 Nov - 1 Dec
*Spooky 2Br Halloween Sleeps 6 |DowntownSalem
Xmas 15% OFF! 37-Greater Boston Cozy Townhouse
Living room connecting with dining and kitchen.

Xmas 15% OFF! 37-Greater Boston Cozy Townhouse

9.2 out of 10, Wonderful, (25)
"Jenny/host was quick to answer all of my questions The only negative aspect of our stay was due to the street traffic on Copeland. It made it hard to sleep at times"
The price is AED 915
AED 1,801 total
includes taxes & fees
8 Dec - 9 Dec
Xmas 15% OFF! 37-Greater Boston Cozy Townhouse
WALK TO WATER & HISTORIC DISTRICT! PRIVATE !!Large first floor apartment
Private kitchen

WALK TO WATER & HISTORIC DISTRICT! PRIVATE !!Large first floor apartment

9.6 out of 10, Exceptional, (66)
"Property and location was perfect .Only minor complaint would be the noisy neighbors above. Walking/stomping back and forth all day and most of the night. It wouldn't at all keep me from staying here again. Highly recommend. "
WALK TO WATER & HISTORIC DISTRICT! PRIVATE !!Large first floor apartment
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, (121)
"The house is located on a quite street near a quaint Downtown Area The house has area for two cars The house was immaculate and very comfortable. The owner Gregg was very welcoming and worked hard to make sure everything was Ok I want to thank him again for letting my family stay in such a beautiful home If you need a place do not hesitate to take this house "
5-bedroom house. Close to airport, bus & train. 10 min from Boston. Sleeps 10.
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.
Don't see what you're looking for?
See all available properties in Winchester
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Winchester

Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93
Private kitchen

Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93

7.4 out of 10, Good, (30)
"I give this place 3 stars, its a nice place with a good amount of room but there are a few issues. Our stay was Monday - Friday, just 2 adults. Pros - lots of room. Cons - no ac. There is a portable ac unit on wheels in the bedroom however, the exhaust vent goes behind a curtain to the window but not outside. There is no way to open the window for the exhaust vent to take the hot air outside so it just pumps all the hot air back into the room. Be prepared to wake up at 7:30am every morning...
Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93
Global Luxury Suites Downtown Boston
Living room

Global Luxury Suites Downtown Boston

4.0 star property
8.0 out of 10, Very Good, (493)
"We enjoyed our stay. It was walkable to Chinatown. Very accessible to subway station. We liked that our room was on the top floor. "
The price is AED 473
AED 993 total
includes taxes & fees
8 Dec - 9 Dec
Global Luxury Suites Downtown Boston
Maverick Suites at 28 Fenway
Lobby sitting area

Maverick Suites at 28 Fenway

3.0 star property
9.0 out of 10, Wonderful, (152)
"Everything good "
The price is AED 485
AED 916 total
includes taxes & fees
1 Dec - 2 Dec
Maverick Suites at 28 Fenway
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.