Winchester Vacation Rentals

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Check prices for these dates

Tonight
8 Aug - 9 Aug
Tomorrow
9 Aug - 10 Aug
This weekend
8 Aug - 10 Aug
Next weekend
15 Aug - 17 Aug

Vacation Rentals in Winchester

Premier Suites - Bay Village
Cozy retreat with a large bed, fireplace, and large windows.

Premier Suites - Bay Village

2.0 star property
6.2 out of 10, (198)
"Great stay and close to my monthly event site so I hope to come back again."
Premier Suites - Bay Village
Maverick Suites at 28 Fenway
Experience modern comfort in this stylish room, featuring a large bed, sleek bar stools, and a touch of greenery.

Maverick Suites at 28 Fenway

3.0 star property
8.8 out of 10, Excellent, (251)
"Great location "
The price is RM583
RM1,084 total
includes taxes & fees
12 Aug - 13 Aug
Maverick Suites at 28 Fenway
Temple Place Suites
Enjoy a comfortable stay in this well-appointed room with a neatly made bed, desk, and seating area.

Temple Place Suites

2.5 star property
7.0 out of 10, Good, (257)
"Great place!"
The price is RM503
RM1,128 total
includes taxes & fees
9 Aug - 10 Aug
Temple Place Suites
Global Luxury Suites Downtown Boston
Relax in our spacious lobby, featuring a central seating area with sofas and a coffee table, and a large glass door leading to the exterior.

Global Luxury Suites Downtown Boston

4.0 star property
8.0 out of 10, Very good, (572)
"Staff was very friendly! "
Global Luxury Suites Downtown Boston
Bay Village Suites
1 bedroom, desk, laptop workspace, free WiFi

Bay Village Suites

2.0 star property
6.4 out of 10, (189)
"I like this place and good location!!"
Bay Village Suites
Crescent Suites Hotel
Relax in a serene outdoor seating area surrounded by lush foliage and a vibrant bush with yellow flowers.

Crescent Suites Hotel

3.0 star property
9.6 out of 10, Exceptional, (1058)
"Well maintained, great location. Really enjoyed our stay!"
Crescent Suites Hotel
907 Main Hotel Central Square, Sonder by Marriott Bonvoy
Enjoy expansive views from the large windows in this open layout room, featuring a circular seating area and contemporary furniture.

907 Main Hotel Central Square, Sonder by Marriott Bonvoy

4.0 star property
8.2 out of 10, Very good, (512)
"Exceptionally friendly and helpful staff."
The price is RM864
RM1,002 total
includes taxes & fees
24 Aug - 25 Aug
907 Main Hotel Central Square, Sonder by Marriott Bonvoy
Maverick Suites at 89 Marion
Stunning entrance with a grand staircase and elegant door, flanked by wooden panels and a glass window.

Maverick Suites at 89 Marion

2.0 star property
8.4 out of 10, Very good, (247)
"Good nights sleep, cozy, nice amenities. "
The price is RM619
RM1,070 total
includes taxes & fees
4 Sept - 5 Sept
Maverick Suites at 89 Marion
Maverick Suites at 245 Newbury St
Traditional townhouses with bay windows and ornate detailing line the street, offering a mix of residential and commercial spaces.

Maverick Suites at 245 Newbury St

2.0 star property
8.2 out of 10, Very good, (139)
"Clean. Great location. "
The price is RM713
RM1,209 total
includes taxes & fees
2 Sept - 3 Sept
Maverick Suites at 245 Newbury St
Sonder by Marriott Bonvoy Pierce Boston Apartments Fenway
Enjoy a panoramic city view from the large windows in this spacious room with a high ceiling.

Sonder by Marriott Bonvoy Pierce Boston Apartments Fenway

4.0 star property
8.8 out of 10, Excellent, (259)
"Great apartment in a super convenient location near Fenway and BU. Easy access, clean, great views. Definitely would stay here again!"
The price is RM1,038
RM1,224 total
includes taxes & fees
10 Aug - 11 Aug
Sonder by Marriott Bonvoy Pierce Boston Apartments Fenway
Maverick Suites at 400 Columbus Ave
Relax in this stylish corner room with a city view, featuring a comfortable reading nook with a small table and stool.

Maverick Suites at 400 Columbus Ave

2.0 star property
7.4 out of 10, Good, (118)
"Property is located in a very nice area. No frill, what they advertise, you get. "
The price is RM410
RM861 total
includes taxes & fees
8 Sept - 9 Sept
Maverick Suites at 400 Columbus Ave
No. 284 Back Bay Hotel, Sonder by Marriott Bonvoy
Relax and socialize on the outdoor terrace with a fire pit, seating area, and stunning city views.

No. 284 Back Bay Hotel, Sonder by Marriott Bonvoy

4.0 star property
9.4 out of 10, Exceptional, (922)
"Beautiful property "
The price is RM875
RM1,032 total
includes taxes & fees
24 Aug - 25 Aug
No. 284 Back Bay Hotel, Sonder by Marriott Bonvoy
Maverick Suites at 40 Temple St
Rows of charming townhouses with large windows and fire escapes line the cobblestone street.

Maverick Suites at 40 Temple St

2.0 star property
7.4 out of 10, Good, (89)
"Very cozy and centrally located. Satellite tv didn’t work. "
The price is RM796
RM1,304 total
includes taxes & fees
7 Sept - 8 Sept
Maverick Suites at 40 Temple St
Global Luxury Suites East Boston
Relax and take in the breathtaking city skyline and water views from our rooftop lounge, featuring comfortable seating and shaded areas.

Global Luxury Suites East Boston

4.0 star property
7.0 out of 10, Good, (161)
"All was great, the appartement itself, the location and not the least the use of the gym, dundeck and pool. Really a great place to enjoy Boston!"
The price is RM846
RM1,458 total
includes taxes & fees
12 Aug - 13 Aug
Global Luxury Suites East Boston
Charlesgate Suites
Experience a comfortable stay in this elegantly designed room with a large bed, bedside tables, and a television.

Charlesgate Suites

3.5 star property
9.4 out of 10, Exceptional, (184)
"Awesome property, conveniently located near everything, especially Fenway. Definitely will stay here again. "
The price is RM957
RM1,831 total
includes taxes & fees
12 Aug - 13 Aug
Charlesgate Suites
The Chester Hotel
Relax in a classic hotel room with a large bed, upholstered bench, and city view.

The Chester Hotel

4.0 star property
9.0 out of 10, Wonderful, (18)
"Had a great stay. Super convenient to Northeastern and shopping/restaurants. "
The price is RM921
RM1,812 total
includes taxes & fees
10 Aug - 11 Aug
The Chester Hotel
The Monty Boston
Relax in a spacious living area with a large L-shaped sofa, dining table, and bookshelf.

The Monty Boston

2.5 star property
9.6 out of 10, Exceptional, (20)
"Everything was great to live in this place! Very spacious and convenient."
The price is RM2,330
RM3,409 total
includes taxes & fees
10 Aug - 11 Aug
The Monty Boston
Sonder by Marriott Bonvoy The Magnolia Apartments Back Bay
Enter a charming brick building with a black-framed entrance door and a beautiful potted plant.

Sonder by Marriott Bonvoy The Magnolia Apartments Back Bay

3.5 star property
8.8 out of 10, Excellent, (68)
"Great place , size of the apartment , very clean"
The price is RM1,249
RM1,474 total
includes taxes & fees
24 Aug - 25 Aug
Sonder by Marriott Bonvoy The Magnolia Apartments Back Bay
Maverick Suites at 402 Columbus Ave
Enjoy cooking in this well-equipped kitchen with a central island and appliances.

Maverick Suites at 402 Columbus Ave

2.5 star property
7.8 out of 10, Good, (55)
"Easy to walk to and from T stations near by. Decently priced and was overall a great place to stay!"
The price is RM515
RM981 total
includes taxes & fees
4 Sept - 5 Sept
Maverick Suites at 402 Columbus Ave
Fairfield Manner
Interior detail

Fairfield Manner

2.0 star property
The price is RM2,114
RM2,842 total
includes taxes & fees
10 Aug - 11 Aug
Fairfield Manner
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

citizenM Boston North Station

citizenM Boston North Station

10/10 Excellent
"🤘"
Daniel 3-night trip
Posted 8 hours ago
citizenM Boston North Station

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?

Family-friendly attractions include Winter Pond, whereas Middlesex Fells Reservation is a spot to enjoy the outdoors. TD Garden and Fenway Park 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.