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Check prices for these dates

In two weeks
8 May - 10 May
In two months
19 Jun - 21 Jun
In three months
17 Jul - 19 Jul
In four months
14 Aug - 16 Aug

Our top choices for Winchester holiday rentals

Apartment (1 Bedroom) | Interior

Apt in Historic Lynn Neighborhood: 2 Mi to Beach!

Apt in Historic Lynn Neighborhood: 2 Mi to Beach!
3.0 star property
Lynn
The price is 1.765.048 ₫
8.034.657 ₫ total
includes taxes & fees
28 Apr - 29 Apr
Apt in Historic Lynn Neighborhood: 2 Mi to Beach!
Premium Apartment | Living area | 24-inch Smart TV with digital channels

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (29 reviews)
"This was a perfect stay. Exactly how described. Highly recommend. "
United States
Yanmarie
The price is 6.045.948 ₫
11.643.593 ₫ total
includes taxes & fees
10 May - 11 May
The Chester Hotel
Front of property

Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.0 star property
Beacon Hill
7.6 out of 10, Good, (110 reviews)
"A phenomenal stay at maverick suites! The location was fantastic, the room was spotless and cozy, and the check-in/out process was a breeze. I’d happily stay here again and recommend to anyone taking a trip to Boston!"
United States
Kendra
The price is 6.496.430 ₫
9.890.241 ₫ total
includes taxes & fees
4 May - 5 May
Maverick Suites at 40 Temple St
Exterior

Maverick Suites at 245 Newbury St

Maverick Suites at 245 Newbury St
2.0 star property
Back Bay
8.2 out of 10, Very good, (165 reviews)
"Great location. Well priced. Its appeals to a specific type of traveler. Overall clean, quiet, solid WiFi services. I had some initial challenges getting in the building, but that was my fault for not checking in and providing the required documents. I would definitely stay again. PS The pizza place right across the street makes a great thin crust pie. "
United States
James
The price is 5.666.594 ₫
8.936.344 ₫ total
includes taxes & fees
4 May - 5 May
Maverick Suites at 245 Newbury St
Front of property

Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (354 reviews)
"Great stay. "
United States
Anna
The price is 4.599.662 ₫
7.861.318 ₫ total
includes taxes & fees
30 Apr - 1 May
Maverick Suites at 28 Fenway
Rooftop terrace

Marriott Vacation Club® at Custom House, Boston

Marriott Vacation Club® at Custom House, Boston
3.5 star property
Downtown Boston
9.4 out of 10, Exceptional, (630 reviews)
"Beautiful hotel and easy access to everything."
United States
Kimberely
The price is 6.919.252 ₫
7.953.681 ₫ total
includes taxes & fees
30 Apr - 1 May
Marriott Vacation Club® at Custom House, Boston
Exterior

Maverick Suites at 402 Columbus Ave

Maverick Suites at 402 Columbus Ave
2.5 star property
South End
8.0 out of 10, Very good, (69 reviews)
"Easy to walk to and from T stations near by. Decently priced and was overall a great place to stay!"
United States
Jordan
The price is 5.097.564 ₫
8.282.244 ₫ total
includes taxes & fees
4 May - 5 May
Maverick Suites at 402 Columbus Ave
Deluxe Double Room, Shared Bathroom | Iron/ironing board, free WiFi, bed sheets

Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.2 out of 10, (266 reviews)
"The building is falling apart, poorly renovated, and it was evident the minimum was done to the unit to attempt to make it presentable. Lumpy floors, peeling wall paper, dirty window sills, door handle falling off, loud stomping from floor above. My partner wouldn't stay there and booked a separate hotel room."
United States
Timothy
The price is 2.726.604 ₫
4.496.940 ₫ total
includes taxes & fees
28 Apr - 29 Apr
Premier Suites - Bay Village
Lobby lounge

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (684 reviews)
"Great staff, clean, and location"
United States
Juan
The price is 4.534.461 ₫
6.393.378 ₫ total
includes taxes & fees
10 May - 11 May
Global Luxury Suites Downtown Boston
Apartment | 2 bedrooms, desk

Coastal Charm Lobster Ch Teau

Coastal Charm Lobster Ch Teau
2.0 star property
Swampscott
The price is 6.603.877 ₫
17.274.934 ₫ total
includes taxes & fees
28 Apr - 29 Apr
Coastal Charm Lobster Ch Teau
Apartment (1 Bedroom) | Interior

1 Mi to Downtown: Salem Vacation Rental!

1 Mi to Downtown: Salem Vacation Rental!
3.0 star property
Salem
10.0 out of 10, Exceptional, (3 reviews)
"Great overall stay! "
United States
Tessa
The price is 3.055.904 ₫
9.622.936 ₫ total
includes taxes & fees
28 Apr - 29 Apr
1 Mi to Downtown: Salem Vacation Rental!
Premium Studio Suite | Premium bedding, desk, iron/ironing board, free WiFi

Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.4 out of 10, Exceptional, (206 reviews)
"The rooms are very spacious and clean. I liked the lighting provided as well."
United States
Hayley
The price is 6.875.784 ₫
12.446.486 ₫ total
includes taxes & fees
10 May - 11 May
Charlesgate Suites
Terrace/patio

Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,176 reviews)
"Excellent stay as always, my home away from home when traveling in the area."
United States
Sean
The price is 3.769.826 ₫
4.210.896 ₫ total
includes taxes & fees
30 Apr - 1 May
Crescent Suites Hotel
Classic Apartment, 3rd floor 3 Bedrooms | 1 bedroom, iron/ironing board, free cots/infant beds, rollaway beds

Apartments in Salem

Apartments in Salem
3.0 star property
Salem
8.0 out of 10, Very good, (48 reviews)
"The whole floor was clean and organized. The whole floor also felt inviting and comforting. We enjoyed how close we where to everthing. We were both so happy with found this apartment. "
United States
Jason
The price is 6.480.624 ₫
11.173.596 ₫ total
includes taxes & fees
28 Apr - 29 Apr
Apartments in Salem
42-inch TV with satellite channels

Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.4 out of 10, Good, (142 reviews)
"Great location!"
United States
Kevin
The price is 5.097.564 ₫
8.282.244 ₫ total
includes taxes & fees
4 May - 5 May
Maverick Suites at 400 Columbus Ave
Interior entrance

Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner
8.4 out of 10, Very good, (282 reviews)
"Very nice and clean room, excellent location"
United States
Diana
The price is 2.845.152 ₫
5.532.134 ₫ total
includes taxes & fees
28 Apr - 29 Apr
Maverick Suites at 89 Marion
Luxury Suite 2 | Living area | Smart TV, Netflix, Hulu, streaming services

The Monty Boston

The Monty Boston
2.5 star property
Downtown Boston
9.6 out of 10, Exceptional, (36 reviews)
"Excellent location, very easy check in process, clean, just as the pictures showed online."
United States
shannon
The price is 15.542.960 ₫
22.408.998 ₫ total
includes taxes & fees
29 Apr - 30 Apr
The Monty Boston
Indoor pool, pool umbrellas, pool loungers

Global Luxury Suites East Boston

Global Luxury Suites East Boston
4.0 star property
East Boston
7.0 out of 10, Good, (186 reviews)
"Perfect location, professional staff, great parking arrangement "
United States
Joli
The price is 4.874.694 ₫
6.784.475 ₫ total
includes taxes & fees
11 May - 12 May
Global Luxury Suites East Boston
Condo (The Warlock House) | Exterior

The Warlock House

The Warlock House
3.0 star property
Salem
The price is 15.077.462 ₫
26.008.391 ₫ total
includes taxes & fees
28 Apr - 29 Apr
The Warlock House
House | 5 bedrooms, desk

Enchanting Hidden Door Escape

Enchanting Hidden Door Escape
2.0 star property
Stoneham
The price is 9.442.559 ₫
20.788.126 ₫ total
includes taxes & fees
28 Apr - 29 Apr
Enchanting Hidden Door Escape
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

Harborside Inn Of Boston

Harborside Inn Of Boston

10/10 Excellent
"Staff was beyond expectations "
Randy 3-night trip
Posted 1 hour ago
Harborside Inn Of Boston

Frequently asked questions

Can I find holiday rentals in Winchester?

Yes, there are holiday rentals in Winchester close to Winter Pond, or you can select a more secluded option if you're looking for a relaxing stay. Winchester is known for its football matches and lake views.

What can I see and do in Winchester?

While exploring the area, visit family-friendly sights like Winter Pond, or get outside and enjoy nature at Boston Common. Fenway Park and Encore Boston Harbor are other popular places to visit in the area.

What are holiday rentals like in Winchester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winchester. Holiday rentals offer amenities such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can provide a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for family trips.