A town with a prominent church, a large building with a clock tower, and a mix of residential and commercial buildings surrounded by greenery.

Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Winchester vacation rentals

An outdoor patio with round tables and chairs, surrounded by green umbrellas.

1. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,297 reviews)
"Property was clean and cozy, convenient to the university and all the restaurants downtown!"
United States
kari
The price is NT$4,846
NT$5,413 total
includes taxes & fees
Oct 31 - Nov 1
Crescent Suites Hotel
A balcony with a city view, featuring a table with wine glasses and a bottle, and a chair.

2. Marriott Vacation Club® at Custom House, Boston

Marriott Vacation Club® at Custom House, Boston
3.5 star property
Downtown Boston
9.6 out of 10, Exceptional, (671 reviews)
"The hotel was beautiful and so unique. Staff was amazing and it was in a great location."
United States
Brittany
The price is NT$13,243
NT$15,223 total
includes taxes & fees
Nov 1 - Nov 2
Marriott Vacation Club® at Custom House, Boston
A modern lobby with a wooden panel wall, a beige sofa, a patterned rug, and a large abstract painting.

3. Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (757 reviews)
"This is my new favorite place to stay in Boston!! Nice location, nice space & amazing opportunities!!"
United States
Myah
The price is NT$5,678
NT$10,359 total
includes taxes & fees
Nov 1 - Nov 2
Global Luxury Suites Downtown Boston
A modern living room with a black leather sofa, grey armchairs, a coffee table, and a large window offering a city view.

4. Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (323 reviews)
"Excellent property upscale amenities full kitchen perfect in every way and my room was only a studio I’ll definitely be back next time to try a larger room just to see what they’re like"
United States
Dirk
The price is NT$7,886
NT$12,361 total
includes taxes & fees
Nov 1 - Nov 2
Kasa Boston at Fenway
A modern living room with a blue wall, a large window, a sofa, a coffee table, and a TV.

5. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (39 reviews)
"It was in a great neighbourhood and beautiful decorated"
United Kingdom
Shanida
The price is NT$6,245
NT$11,207 total
includes taxes & fees
Oct 4 - Oct 5
The Chester Hotel
A wooden hallway with a patterned floor leading to a door.

6. Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner
8.4 out of 10, Very good, (326 reviews)
"Room was clean, neat area."
United States
Keir
The price is NT$4,409
NT$7,772 total
includes taxes & fees
Oct 4 - Oct 5
Maverick Suites at 89 Marion
A row of multi-story brick buildings with a central entrance, a flag, and parked cars on the street.

7. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (434 reviews)
"Comfortable room, walkable area, beautiful park across the road, and easy to work with."
United States
Amber
The price is NT$4,273
NT$8,024 total
includes taxes & fees
Nov 1 - Nov 2
Maverick Suites at 28 Fenway
A modern hotel room with a bed, a desk, a sofa, and a dining area.

8. Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.2 out of 10, Wonderful, (239 reviews)
"Great location if you go to the BCH"
Mexico
Ana
The price is NT$6,468
NT$12,929 total
includes taxes & fees
Oct 4 - Oct 5
Charlesgate Suites
A row of brick buildings with storefronts, including a bakery and a liquor store.

9. 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, (206 reviews)
"Right in the heart of the shopping district, easy walking and central to Fenway/downtown Boston"
United States
Jennifer
The price is NT$4,194
NT$7,751 total
includes taxes & fees
Oct 4 - Oct 5
Maverick Suites at 245 Newbury St
A row of brick townhouses with fire escapes, a brick sidewalk, and potted plants.

10. Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.5 star property
Beacon Hill
7.8 out of 10, Good, (151 reviews)
"There only a few things I require from a hotel. Hotel Maverick Suites at 40 are clean, quiet and reasonably priced. I enjoyed my stay there immensely. A bonus was their convenient location."
United States
Jerrold
The price is NT$3,699
NT$7,182 total
includes taxes & fees
Nov 1 - Nov 2
Maverick Suites at 40 Temple St
Room

11. Symple Live

Symple Live
4.5 star property
Fenway–Kenmore
9.2 out of 10, Wonderful, (27 reviews)
"Great location. Exactly as pictured."
United States
Erica
The price is NT$9,176
NT$14,027 total
includes taxes & fees
Nov 1 - Nov 2
Symple Live
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

8/10 Good
"Everything good but no TV the first evening and no coffeemaker in room."
Marjorie 3-night trip
Posted less than an hour ago
Harborside Inn Of Boston

Find out more about Winchester

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

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Frequently asked questions

Can I find vacation rentals in Winchester?

Yes, we have vacation rentals in Winchester close to Winter Pond, or you can choose a more remote option if you're looking for a relaxing stay. Winchester is known for its soccer matches and lake views.

How many vacation rentals are there in Winchester?

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

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 vacation rentals like in Winchester?

Vacation rentals are privately owned properties you can book for a few days or a quick weekend in Winchester. Vacation rentals feature extras like laundry facilities and kitchens so you'll feel right at home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a family trip.