Winchester Vacation Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Winchester holiday rentals

A modern lobby with a wooden panel wall, a beige sofa, a patterned rug, and a large abstract painting.

1. Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (774 reviews)
"Great room: new and spacious. The kitchenette has everything i needed and more."
United States
Yelitza
The price is RM409
RM949 total
includes taxes & fees
7 Dec - 8 Dec
Global Luxury Suites Downtown Boston
An outdoor patio with round tables and chairs, surrounded by green umbrellas.

2. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,354 reviews)
"Wehave stayed here several times and each time has been a pleasure."
United States
Kasandra
The price is RM617
RM689 total
includes taxes & fees
11 Nov - 12 Nov
Crescent Suites Hotel
A row of multi-story brick buildings with a central entrance, a flag, and parked cars on the street.

3. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (477 reviews)
"Great location and the room was nicely decorated and clean!"
United States
Judy
The price is RM410
RM868 total
includes taxes & fees
11 Nov - 12 Nov
Maverick Suites at 28 Fenway
A wooden hallway with a patterned floor leading to a door.

4. Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner
8.4 out of 10, Very good, (356 reviews)
"The area was walkable and the room was great!"
United States
Edna
The price is RM321
RM721 total
includes taxes & fees
17 Nov - 18 Nov
Maverick Suites at 89 Marion
A row of brick buildings with storefronts, including a bakery and a liquor store.

5. Maverick Suites at 245 Newbury St

Maverick Suites at 245 Newbury St
2.0 star property
Back Bay
8.4 out of 10, Very good, (219 reviews)
"Great location - plenty to do."
United States
Chloe
The price is RM358
RM785 total
includes taxes & fees
6 Dec - 7 Dec
Maverick Suites at 245 Newbury St
A row of brick townhouses with fire escapes, a brick sidewalk, and potted plants.

6. Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.5 star property
Beacon Hill
8.0 out of 10, Very good, (167 reviews)
"great location near the commons. nice space for single traveler."
United States
Andrea
The price is RM287
RM703 total
includes taxes & fees
1 Dec - 2 Dec
Maverick Suites at 40 Temple St
A modern bedroom with a large bed, a fireplace, and two windows with blinds.

7. Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.4 out of 10, (399 reviews)
"Good place to stay."
United States
Jaetaek
The price is RM343
RM605 total
includes taxes & fees
23 Nov - 24 Nov
Premier Suites - Bay Village
A spacious indoor swimming pool with large windows, modern seating, and a wooden ceiling.

8. Global Luxury Suites East Boston

Global Luxury Suites East Boston
4.0 star property
East Boston
6.8 out of 10, (216 reviews)
"Cozy, comfy and cute✨. Would def rent again❤️"
United States
Erica
The price is RM503
RM1,045 total
includes taxes & fees
6 Dec - 7 Dec
Global Luxury Suites East Boston
A hotel room with a bed, two bedside lamps, a window with blinds, and a framed picture on the wall.

9. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, Good, (556 reviews)
"We will definitely stay here again!"
United States
James
The price is RM365
RM676 total
includes taxes & fees
1 Dec - 2 Dec
Temple Place Suites
A modern living room with a blue wall, a large window, a sofa, a coffee table, and a TV.

10. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (45 reviews)
"I had a great stay at The Chester Hotel. Super cute vibe, easy check-in, and good location for where I needed to be for work. Bed is super comfy, the room aesthetic is great and the restaurant MIDA next door was really good!"
United States
Tracy
The price is RM584
RM1,185 total
includes taxes & fees
11 Nov - 12 Nov
The Chester Hotel
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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Find out more about Winchester

Search for holiday rentals in Winchester on Expedia.co.uk! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

  • View our selection of featured holiday rentals in Winchester
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Look no further and take a look at our great range of rental properties in Winchester!

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.

How many holiday rentals are there in Winchester?

Choose from 3 Expedia holiday rentals in Winchester for a memorable holiday.

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.

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