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 vacation rentals

A pathway leading to a stone bench surrounded by trees with yellow leaves. A sign requests the use of the sidewalk for access to Charles River.

1. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,357 reviews)
"Wehave stayed here several times and each time has been a pleasure."
United States
Kasandra
The price is AEDĀ 503
AEDĀ 562 total
includes taxes & fees
15 Dec - 16 Dec
Crescent Suites Hotel
A narrow brick pathway flanked by white buildings with green plants and Christmas decorations.

2. 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, (19 reviews)
"Great stay and great host! Would come back! Area is super safe and lovely!"
United States
I A.
The price is AEDĀ 496
AEDĀ 927 total
includes taxes & fees
15 Nov - 16 Nov
Charming 1-bedroom well located Garden Apartment in Historic West Medford
A stone house with a garden bed, a hose, and a brick pathway.

3. Garden Bliss Studio

Garden Bliss Studio
Medford
10.0 out of 10, Exceptional, (68 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 AEDĀ 364
AEDĀ 853 total
includes taxes & fees
15 Nov - 16 Nov
Garden Bliss Studio
A two-story house with a front porch, a chimney, and a mailbox.

4. Enchanting Hidden Door Escape

Enchanting Hidden Door Escape
Stoneham
9.6 out of 10, Exceptional, (37 reviews)
"Property was very nice! Updated and clean!"
United States
Aimee M.
The price is AEDĀ 912
AEDĀ 2,240 total
includes taxes & fees
24 Nov - 25 Nov
Enchanting Hidden Door Escape
A balcony with a city view, featuring a table with wine glasses and a bottle, and a chair.

5. Marriott Vacation ClubĀ® at Custom House, Boston

Marriott Vacation ClubĀ® at Custom House, Boston
3.5 star property
Downtown Boston
9.4 out of 10, Exceptional, (682 reviews)
"Nice hotel with a great location. Rooms were very spacious with many amenities to offer. Will definitely be back again."
United States
Joseph
The price is AEDĀ 859
AEDĀ 987 total
includes taxes & fees
29 Nov - 30 Nov
Marriott Vacation ClubĀ® at Custom House, Boston
A two-story house with a front porch, a staircase, and a flower pot with purple flowers.

6. Near Boston Historic two-bedroom with Modern Amenities

Near Boston Historic two-bedroom with Modern Amenities
Malden
10.0 out of 10, Exceptional, (339 reviews)
"This property is gorgeous! No need for anything once you arrive because it has everything!! The owner is great at communicating and accommodating. If you are in the Boston area and want a comfortable, safe and lovely place to stay this is it. Canā€™t wait to visit again!"
United States
Lesley M.
The price is AEDĀ 744
AEDĀ 1,028 total
includes taxes & fees
15 Nov - 16 Nov
Near Boston Historic two-bedroom with Modern Amenities
A white door with a window, a welcome sign, and a black trash bin.

7. Boston 2bd King Bed near Harvard, MIT, subway near Boston. On-site free Parking

Boston 2bd King Bed near Harvard, MIT, subway near Boston. On-site free Parking
Ward Two
10.0 out of 10, Exceptional, (27 reviews)
"Great place close to places of interest. Walking distance to Dali - a Spanish Tapas restaurant that is authentic and delicious. Enjoyed our stay."
United States
Mike M.
The price is AEDĀ 391
AEDĀ 1,023 total
includes taxes & fees
15 Nov - 16 Nov
Boston 2bd King Bed near Harvard, MIT, subway near Boston. On-site free Parking
A wooden deck with a white railing, two large planters with various plants, and a wooden chair.

8. 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, (157 reviews)
"We enjoyed our stay! Great location, easy parking. Wonderful communication from host. Would stay again!"
United States
Martha W.
The price is AEDĀ 872
AEDĀ 2,029 total
includes taxes & fees
16 Nov - 17 Nov
5-bedroom house. Close to airport, bus & train. 10 min from Boston. Sleeps 10.
A modern living room with large windows, a sofa, a coffee table, and a lamp.

9. Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenwayā€“Kenmore
9.0 out of 10, Wonderful, (352 reviews)
"Great location, very comfortable apartment, great facilities, everyone was friendly and helpful!!!"
United States
antonio
The price is AEDĀ 661
AEDĀ 1,091 total
includes taxes & fees
23 Nov - 24 Nov
Kasa Boston at Fenway
A multi-story hotel with a classic architectural style, featuring arched windows and a central entrance.

10. Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (776 reviews)
"Great room: new and spacious. The kitchenette has everything i needed and more."
United States
Yelitza
The price is AEDĀ 342
AEDĀ 826 total
includes taxes & fees
13 Dec - 14 Dec
Global Luxury Suites Downtown Boston
A modern living room with a blue wall, a large window, a sofa, a coffee table, and a TV.

11. 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 AEDĀ 453
AEDĀ 985 total
includes taxes & fees
23 Nov - 24 Nov
The Chester Hotel
A kitchen with a stainless steel sink, white cabinets, and a green tiled backsplash.

12. NEW Modern Apartment Near Boston & Harvard Square.

NEW Modern Apartment Near Boston & Harvard Square.
Watertown
10.0 out of 10, Exceptional, (55 reviews)
"That was the most comfortable bed I have slept in away from home!"
United States
Kimberly M.
NEW Modern Apartment Near Boston & Harvard Square.
A wooden hallway with a patterned floor leading to a door.

13. Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner
8.4 out of 10, Very good, (357 reviews)
"The area was walkable and the room was great!"
United States
Edna
The price is AEDĀ 291
AEDĀ 653 total
includes taxes & fees
15 Nov - 16 Nov
Maverick Suites at 89 Marion
A row of multi-story brick buildings with a central entrance, a flag, and parked cars on the street.

14. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenwayā€“Kenmore
8.6 out of 10, Excellent, (479 reviews)
"Great location and the room was nicely decorated and clean!"
United States
Judy
The price is AEDĀ 372
AEDĀ 786 total
includes taxes & fees
15 Nov - 16 Nov
Maverick Suites at 28 Fenway
A modern kitchen with white cabinets, stainless steel appliances, and a central island with a flower arrangement.

15. 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, (31 reviews)
"Beautiful unit with attentive host and safe parking. We enjoyed our stay."
United States
Debbie L.
The price is AEDĀ 602
AEDĀ 1,608 total
includes taxes & fees
15 Nov - 16 Nov
3BR2Bth TD Garden/MIT/Harvard/BOS/3 Parking Spaces
A row of brick buildings with storefronts, including a bakery and a liquor store.

16. 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 AEDĀ 317
AEDĀ 703 total
includes taxes & fees
6 Dec - 7 Dec
Maverick Suites at 245 Newbury St
A modern hotel room with a bed, a desk, a sofa, and a dining area.

17. Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenwayā€“Kenmore
9.2 out of 10, Wonderful, (247 reviews)
"Spacers, convenient location"
United States
Svetlana
The price is AEDĀ 632
AEDĀ 1,360 total
includes taxes & fees
23 Nov - 24 Nov
Charlesgate Suites
A building with a sign reading "GREEN TURTLE" and a dock with red chairs.

18. 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, (268 reviews)
"The Houseboat was well appointed and clean. The hosts were very kind and left various drinks and breakfast items for us to enjoy. We enjoyed our stay there."
United States
D K
The price is AEDĀ 988
AEDĀ 1,782 total
includes taxes & fees
15 Nov - 16 Nov
Romantic Boston Harbor Houseboat Stay for 2 people. A/C. Close to Freedom Trail.
A hallway with a welcome sign, a kitchen area with a counter and stools, and a patterned rug.

19. Bee-Themed Stay Near Boston ā€“ A Sweet and Unique Getaway

Bee-Themed Stay Near Boston ā€“ 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 AEDĀ 407
AEDĀ 789 total
includes taxes & fees
15 Nov - 16 Nov
Bee-Themed Stay Near Boston ā€“ A Sweet and Unique Getaway
A row of brick townhouses with fire escapes, a brick sidewalk, and potted plants.

20. 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, (169 reviews)
"great location near the commons. nice space for single traveler."
United States
Andrea
The price is AEDĀ 260
AEDĀ 636 total
includes taxes & fees
1 Dec - 2 Dec
Maverick Suites at 40 Temple St
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

A spacious lobby with a mix of seating areas, a fireplace, and large windows providing natural light.
Archer Hotel Boston/Burlington

Archer Hotel Boston/Burlington

Archer Hotel Boston/Burlington
Burlington

10/10 Excellent

My boyfriend and I stayed for Valentineā€™s Day and upon arriving we were greeted with kindness and 2 glasses of champagne! Check in was perfect. The room was perfect. Definitely one of my favorite hotels for sure. We also ate at my favorite restaurant right 10 steps across the street! We could literally see the entrance right from our room window. It was a beautiful experience here.
United States
Desiree
Reviewed February 15, 2025
Archer Hotel Boston/Burlington

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.