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
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Winchester vacation rentals

Property grounds

1. Garden Studio, access to I-93 to Airport, Tufts U, Hiking & Chevalier Theater.

Garden Studio, access to I-93 to Airport, Tufts U, Hiking & Chevalier Theater.
Medford
10.0 out of 10, Exceptional, (64 reviews)
"Excellent communication with hosts, perfect location for so many sites in the region, lovely space just as advertised. "
United States
Lynn C.
$235 nightly
The price is $262
Aug 12 - Aug 13
Total with taxes and fees
Garden Studio, access to I-93 to Airport, Tufts U, Hiking & Chevalier Theater.
Premium Apartment | Living area | 24-inch Smart TV with digital channels

2. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (36 reviews)
"It was in a great neighbourhood and beautiful decorated"
United Kingdom
Shanida
$261 nightly
The price is $300
Aug 12 - Aug 13
Total with taxes and fees
The Chester Hotel
Exterior

3. Free Parking at 1 Bed Basement Apt, Near BU & MIT

Free Parking at 1 Bed Basement Apt, Near BU & MIT
Fenway–Kenmore
8.4 out of 10, Very Good, (29 reviews)
"Friendly hosts"
United States
Jan
$199 nightly
The price is $217
Aug 13 - Aug 14
Total with taxes and fees
Free Parking at 1 Bed Basement Apt, Near BU & MIT
Exterior

4. Light-filled Studio | Back Bay

Light-filled Studio | Back Bay
Back Bay
9.6 out of 10, Exceptional, (9 reviews)
"Perfect location! On a quiet street right in the heart of the Back Bay. Can easily walk to restaurants, grocery stores, the Prudential Center, and pubic transportation. Close to the nearby colleges which was helpful for our stay. We were able to support our college-age kid through a tough moment. It was clean, comfortable, and management was responsive and friendly. It was easy in and out. We’ll definitely come back. This would be perfect if you had any kind of medical emergency or needed to...
United States
Gretchen J.
$248 nightly
The price is $320
Aug 19 - Aug 20
Total with taxes and fees
Light-filled Studio | Back Bay
Front of property

5. Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.0 star property
Beacon Hill
7.8 out of 10, Good, (141 reviews)
"Worth the stay"
Canada
Akansha
$236 nightly
The price is $271
Aug 12 - Aug 13
Total with taxes and fees
Maverick Suites at 40 Temple St
1 Queen Bed with Sofa Bed (6th Floor - Elevator stops on 5th then stairs up) | Desk, iron/ironing board, WiFi (free), bed sheets

6. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.0 out of 10, Good, (433 reviews)
"Great location so close to everything"
United States
Hunter
$164 nightly
The price is $189
Aug 12 - Aug 13
Total with taxes and fees
Temple Place Suites
Exterior

7. 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, (197 reviews)
"Location was perfect! The room was great and exactly what I needed for my business trip"
United States
Michael
$246 nightly
The price is $283
Aug 18 - Aug 19
Total with taxes and fees
Maverick Suites at 245 Newbury St
1 bedroom, desk, iron/ironing board, internet

8. Cozy Studio Steps from Boston Common and Theaters

Cozy Studio Steps from Boston Common and Theaters
Bay Village
7.6 out of 10, Good, (15 reviews)
"All good, would definitely stay again"
United States
Dan C.
$235 nightly
The price is $276
Aug 16 - Aug 17
Total with taxes and fees
Cozy Studio Steps from Boston Common and Theaters
2 bedrooms, WiFi, bed sheets

9. Great Apartment on River/ Harvard Square two blocks

Great Apartment on River/ Harvard Square two blocks
West Cambridge
8.6 out of 10, Excellent, (38 reviews)
"Perfect location to explore Cambridge."
United States
Anonymous traveler
$280 nightly
The price is $321
Aug 12 - Aug 13
Total with taxes and fees
Great Apartment on River/ Harvard Square two blocks
Coffee/tea maker, fridge, microwave, oven

10. 3BR2Bth TD Garden/MIT/Harvard/BOS/3 Parking Spaces

3BR2Bth TD Garden/MIT/Harvard/BOS/3 Parking Spaces
East Somerville
10.0 out of 10, Exceptional, (28 reviews)
"Beautiful unit with attentive host and safe parking. We enjoyed our stay."
United States
Debbie L.
$365 nightly
The price is $407
Aug 16 - Aug 17
Total with taxes and fees
3BR2Bth TD Garden/MIT/Harvard/BOS/3 Parking Spaces
Smart TV, books

11. Bright 2BR by Boston Waterfront

Bright 2BR by Boston Waterfront
East Boston
9.6 out of 10, Exceptional, (40 reviews)
"7 min from the airport, seamless check in and entry and a spotless, welcoming place- with coffee! Great rental- perfect if you’re coming/going from Logan"
United States
Bridget
$270 nightly
The price is $310
Aug 12 - Aug 13
Total with taxes and fees
Bright 2BR by Boston Waterfront
Studio | Iron/ironing board, WiFi (free)

12. The Concord Hotel

The Concord Hotel
2.0 star property
South End
7.0 out of 10, Good, (12 reviews)
"Clean room and linens, great location and comfortable bed. Only complaint is the street noise and sounds from residents in upstairs apartment which was kind of loud. All things considered I’d stay again as it was a good value spot"
United States
Nancy
$252 nightly
The price is $290
Aug 12 - Aug 13
Total with taxes and fees
The Concord Hotel
Terrace/patio

13. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,245 reviews)
"Dana is a great host, nice spacious rooms"
United States
joseph
$179 nightly
The price is $200
Aug 12 - Aug 13
Total with taxes and fees
Crescent Suites Hotel
Exterior

14. Walk everywhere - Seaport, North End, Beacon Hill. Steps from MBTA public transit. Keyless Entry!

Walk everywhere - Seaport, North End, Beacon Hill. Steps from MBTA public transit. Keyless Entry!
Downtown Boston
9.0 out of 10, Wonderful, (2 reviews)
"Host was very communicative. The apartment was very clean and spacious and the location was fantastic! A lot of things in walking distance and train stop nearby for getting to other parts of the city was convenient. I would highly recommend this host and their space! Thank you for your hospitality! Would love to come back."
United States
Rachael M.
$276 nightly
The price is $356
Aug 20 - Aug 21
Total with taxes and fees
Walk everywhere - Seaport, North End, Beacon Hill. Steps from MBTA public transit. Keyless Entry!
Front of property

15. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (402 reviews)
"Easy to move-in, location is good for traveler. The shower room not that clean, some hair from previous guests, just clean it can be manage by guest."
Taiwan
LICHIEH
$236 nightly
The price is $271
Aug 12 - Aug 13
Total with taxes and fees
Maverick Suites at 28 Fenway
Deluxe Double Room, Shared Bathroom | Iron/ironing board, WiFi (free), bed sheets

16. Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.4 out of 10, (324 reviews)
"Lovely small property with thoughtful touches like cool water bottles & Nespresso available 24hrs. I had to take a last minute Zoom call and the front desk reserved the business center room for me. The rooms themselves are a bit small but very comfortable beds and linens."
United States
Theresa
$154 nightly
The price is $177
Aug 12 - Aug 13
Total with taxes and fees
Premier Suites - Bay Village
1 bedroom, iron/ironing board, WiFi, bed sheets

17. Primo North End Studio

Primo North End Studio
North End
9.4 out of 10, Exceptional, (19 reviews)
"Great place, amazing location!"
United States
Christopher W.
$303 nightly
The price is $348
Aug 16 - Aug 17
Total with taxes and fees
Primo North End Studio
Premium Studio Suite | Premium bedding, desk, iron/ironing board, WiFi (free)

18. Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.2 out of 10, Wonderful, (224 reviews)
"Very nice room and close to fenway"
United States
timothy
$328 nightly
The price is $377
Aug 16 - Aug 17
Total with taxes and fees
Charlesgate Suites
1 bedroom, desk, iron/ironing board, WiFi

19. Downtown Studio | Students Welcome | W/D in unit

Downtown Studio | Students Welcome | W/D in unit
Downtown Boston
9.4 out of 10, Exceptional, (3 reviews)
"Was worth the price all around"
United States
steven l.
$253 nightly
The price is $326
Aug 18 - Aug 19
Total with taxes and fees
Downtown Studio | Students Welcome | W/D in unit
42-inch TV with satellite channels

20. Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.4 out of 10, Good, (161 reviews)
"Well located"
United States
Evelyn
$233 nightly
The price is $258
Aug 13 - Aug 14
Total with taxes and fees
Maverick Suites at 400 Columbus Ave
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 Back Bay

citizenM Boston Back Bay

10/10 Excellent
"Small, cozy room but with a good view, just the way I like it! Close to the subway and newbury street for shopping!"
Alexandra 3-night trip
Posted less than an hour ago
citizenM Boston Back Bay

Find out more about Winchester

Everything you need to know about Winchester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winchester vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchester. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winchester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $177 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find vacation rentals in Winchester?

Yes, we have vacation rentals in Winchester close to Griffin Photography Museum, 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.

What are some of the best vacation home rentals in Winchester?

Lorenzo Inn: This vacation home rental outside of Winchester offers a garden, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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. TD Garden and Fenway Park 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.