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

Our top choices for Winchester vacation rentals

A residential house with a covered porch, a garage, and a well-maintained garden.

1. Charming 1-bedroom well located Garden Apartment in Historic West Medford

Charming 1-bedroom well located Garden Apartment in Historic West Medford
West Medford
10.0 out of 10, Exceptional, (15 reviews)
"Will not be disappointed!"
United States
Dave O.
The price is AED 588
AED 1,047 total
includes taxes & fees
30 Sep - 1 Oct
Charming 1-bedroom well located Garden Apartment in Historic West Medford
A stone house with a garden bed, a hose, and a brick pathway.

2. 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, (66 reviews)
"Excellent place to stay in Medford. Everything was great and we ended up only had two persons staying here, for which it was great!"
United States
Michael C.
The price is AED 529
AED 1,022 total
includes taxes & fees
5 Oct - 6 Oct
Garden Studio, access to I-93 to Airport, Tufts U, Hiking & Chevalier Theater.
An outdoor patio with round tables and chairs, surrounded by green umbrellas.

3. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,292 reviews)
"The full kitchen is amazing. The laundry soap provided was a nice surprise! It’s clean, quiet and gives a home like feeling for a hotel."
United States
Mrs. Andrea
The price is AED 592
AED 661 total
includes taxes & fees
4 Oct - 5 Oct
Crescent Suites Hotel
A staircase with white balusters and a wooden handrail, leading to a landing with a lamp and a small table.

4. 5-bedroom house. Close to airport, bus & train. 10 min from Boston. Sleeps 10.

5-bedroom house. Close to airport, bus & train. 10 min from Boston. Sleeps 10.
Melrose
10.0 out of 10, Exceptional, (153 reviews)
"We enjoyed our stay! The house is beautiful, clean and as described. Greg was extremely helpful and very quick to respond. Neighborhood felt safe and would definitely stay again!"
United States
KATIE G.
The price is AED 909
AED 1,939 total
includes taxes & fees
30 Sep - 1 Oct
5-bedroom house. Close to airport, bus & train. 10 min from Boston. Sleeps 10.
A spacious living room with a dining area, wooden columns, and a large window providing natural light.

5. Near Boston Historic two-bedroom with Modern Amenities

Near Boston Historic two-bedroom with Modern Amenities
Malden
10.0 out of 10, Exceptional, (329 reviews)
"Place was spotless and had everything you needed for a great stay."
United States
Jenn K.
The price is AED 734
AED 1,025 total
includes taxes & fees
30 Sep - 1 Oct
Near Boston Historic two-bedroom with Modern Amenities
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, (320 reviews)
"Room was clean, neat area."
United States
Keir
The price is AED 508
AED 896 total
includes taxes & fees
1 Oct - 2 Oct
Maverick Suites at 89 Marion
A living room with a sofa, a glass coffee table, a TV mounted on the wall, a wooden floor, and a window with a view of trees.

7. NEW Modern Apartment Near Boston & Harvard Square.

NEW Modern Apartment Near Boston & Harvard Square.
Watertown
10.0 out of 10, Exceptional, (53 reviews)
"That was the most comfortable bed I have slept in away from home!"
United States
Kimberly M.
The price is AED 455
AED 796 total
includes taxes & fees
25 Oct - 26 Oct
NEW Modern Apartment Near Boston & Harvard Square.
A living room with a grey sofa, a black armchair, a coffee table, and a blue rug. There are two windows with blinds, a bookshelf, and a potted plant.

8. Bright 2BR by Boston Waterfront

Bright 2BR by Boston Waterfront
East Boston
9.8 out of 10, Exceptional, (44 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
The price is AED 536
AED 1,270 total
includes taxes & fees
4 Oct - 5 Oct
Bright 2BR by Boston Waterfront
A hallway with a welcome sign, a kitchen area with a counter and stools, and a patterned rug.

9. Bee-Themed Stay Near Boston – A Sweet and Unique Getaway

Bee-Themed Stay Near Boston – A Sweet and Unique Getaway
Billerica
10.0 out of 10, Exceptional, (17 reviews)
"It was a great stay. The place was cosy and had everything you need and stuff you forgot to bring . I will definitely be staying here again."
United States
Jonathan
The price is AED 670
AED 1,098 total
includes taxes & fees
11 Oct - 12 Oct
Bee-Themed Stay Near Boston – A Sweet and Unique Getaway
A modern kitchen with dark cabinets, a white countertop, stainless steel appliances, and a central island with bar stools.

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, (30 reviews)
"Beautiful unit with attentive host and safe parking. We enjoyed our stay."
United States
Debbie L.
The price is AED 595
AED 1,584 total
includes taxes & fees
4 Oct - 5 Oct
3BR2Bth TD Garden/MIT/Harvard/BOS/3 Parking Spaces
A wooden building entrance with two lanterns, a paved path, and a tree with pink leaves in the background.

11. Heart Cambridge free parking 1 bedroom MIT/Harvard/ Boston/4#

Heart Cambridge free parking 1 bedroom MIT/Harvard/ Boston/4#
Cambridgeport
9.4 out of 10, Exceptional, (44 reviews)
"Very friendly and easy walk to fenway"
United States
thomas p.
The price is AED 694
AED 1,257 total
includes taxes & fees
14 Oct - 15 Oct
Heart Cambridge free parking 1 bedroom MIT/Harvard/ Boston/4#
A modern bedroom with a large bed, a fireplace, and two windows with blinds.

12. Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.4 out of 10, (352 reviews)
"Location is great"
United States
Eria
The price is AED 443
AED 699 total
includes taxes & fees
30 Sep - 1 Oct
Premier Suites - Bay Village
A bedroom with a bed, a round table with chairs, a TV, and a large mirror.

13. The Concord Hotel

The Concord Hotel
2.0 star property
South End
7.6 out of 10, Good, (25 reviews)
"Great room! Cool place to stay. We walked everywhere and stuff was close by. Woud stay here again"
United States
Cotie
The price is AED 677
AED 1,242 total
includes taxes & fees
30 Sep - 1 Oct
The Concord Hotel
A modern living room with a blue wall, a large window, a sofa, a coffee table, and a TV.

14. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (38 reviews)
"It was in a great neighbourhood and beautiful decorated"
United Kingdom
Shanida
The price is AED 606
AED 1,161 total
includes taxes & fees
30 Sep - 1 Oct
The Chester Hotel
A hotel room with a bed, two bedside lamps, a window with blinds, and a framed picture on the wall.

15. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, Good, (484 reviews)
"Clean, good location, all what I need for short stay"
United States
Julia
The price is AED 463
AED 764 total
includes taxes & fees
29 Oct - 30 Oct
Temple Place Suites
A white table with a vase of white orchids, a white chair, and a view of a cityscape through a window with a black frame.

16. Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.6 out of 10, Good, (175 reviews)
"Well located"
United States
Evelyn
The price is AED 536
AED 953 total
includes taxes & fees
30 Sep - 1 Oct
Maverick Suites at 400 Columbus Ave
A hallway with brick walls and a polished floor, leading to a door.

17. Enjoyable 2-bedroom lower level apartment in charming Lynn

Enjoyable 2-bedroom lower level apartment in charming Lynn
Lynn
9.0 out of 10, Wonderful, (27 reviews)
"NICE PLACE TO USE AS A BASE TO SEE TO TRAVEL FROM"
United States
Rodney S.
The price is AED 364
AED 741 total
includes taxes & fees
29 Oct - 30 Oct
Enjoyable 2-bedroom lower level apartment in charming Lynn
A brick building with a black front door, a staircase, and a well-maintained garden.

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

Free Parking at 1 Bed Basement Apt, Near BU & MIT
Fenway–Kenmore
8.6 out of 10, Excellent, (37 reviews)
"Friendly hosts"
United States
Jan
The price is AED 437
AED 881 total
includes taxes & fees
7 Oct - 8 Oct
Free Parking at 1 Bed Basement Apt, Near BU & MIT
A row of brick buildings with storefronts, including a bakery and a liquor store.

19. 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, (205 reviews)
"Right in the heart of the shopping district, easy walking and central to Fenway/downtown Boston"
United States
Jennifer
The price is AED 759
AED 1,236 total
includes taxes & fees
5 Oct - 6 Oct
Maverick Suites at 245 Newbury St
A building with a sign reading "GREEN TURTLE" and a dock with red chairs.

20. Romantic Boston Harbor Houseboat Stay for 2 people. A/C. Close to Freedom Trail.

Romantic Boston Harbor Houseboat Stay for 2 people. A/C. Close to Freedom Trail.
Charlestown
10.0 out of 10, Exceptional, (258 reviews)
"Loved this experience!!! Would book this again! So convenient to see Boston! "
United States
Ellen Z.
The price is AED 998
AED 1,684 total
includes taxes & fees
7 Oct - 8 Oct
Romantic Boston Harbor Houseboat Stay for 2 people. A/C. Close to Freedom Trail.
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

Arcadian Hotel

Arcadian Hotel

8/10 Good
"Staff was friendly and helpful. Lobby was highly utilized, but the breakfast was underwhelming. Plain bagels, dry cereal and bananas.."
Julie 3-night trip
Posted 8 hours ago
Arcadian Hotel

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.

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

Lovely Bright and Spacious 4-bedroom house with 6 off-street parking spots: This vacation home rental outside of Winchester offers a patio, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a hot tub and a selection of books.

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.