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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Our top choices for Winchester vacation rentals

Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.0 out of 10, Good, (397 reviews)
"Wonderful stay at this property. Location was excellent, and the host is very quick and responsive to answer any questions you may have."
United States
Jennifer
The price is AED 360
AED 646 total
includes taxes & fees
30 Jun - 1 Jul
Temple Place Suites

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
10.0 out of 10, Exceptional, (1 review)
"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.
The price is AED 447
AED 1,229 total
includes taxes & fees
5 Jul - 6 Jul
Walk everywhere - Seaport, North End, Beacon Hill. Steps from MBTA public transit. Keyless Entry!

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.6 out of 10, Excellent, (33 reviews)
"Charming room, fresh towels, clean!! I would stay here again."
United States
Mary
The price is AED 588
AED 1,140 total
includes taxes & fees
30 Jun - 1 Jul
The Chester Hotel

The Concord Hotel

The Concord Hotel
2.0 star property
South End
10.0 out of 10, Exceptional, (1 review)
"Overall had a great experience here. Took just a couple minutes texting the host to get the check in information that was to be emailed- but they sent it pretty quickly when I said it wasn't sent yet. I didn't need anything else from the host. It was clean and overall pretty nice! The stairs you take to get up to the room are pretty loud, so I woke up one time when other people got home to other rooms during my stay, but that was it! Overall good. I was there for a holiday weekend so the price...
United States
Jessica
The price is AED 602
AED 1,157 total
includes taxes & fees
30 Jun - 1 Jul
The Concord Hotel

Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.4 out of 10, (297 reviews)
"Great location and well maintained"
United States
EDDIE
The price is AED 360
AED 604 total
includes taxes & fees
30 Jun - 1 Jul
Premier Suites - Bay Village

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, (23 reviews)
"Friendly hosts"
United States
Jan
The price is AED 349
AED 796 total
includes taxes & fees
2 Jul - 3 Jul
Free Parking at 1 Bed Basement Apt, Near BU & MIT

Light-filled Studio | Back Bay

Light-filled Studio | Back Bay
Back Bay
10.0 out of 10, Exceptional, (3 reviews)
"It was a great stay!"
United States
Adina S.
The price is AED 294
AED 911 total
includes taxes & fees
5 Jul - 6 Jul
Light-filled Studio | Back Bay

Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (378 reviews)
"Great stay. "
United States
Anna
The price is AED 334
AED 743 total
includes taxes & fees
1 Jul - 2 Jul
Maverick Suites at 28 Fenway

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, (176 reviews)
"Room was clean and near the shops of Back Bay"
United States
Steven
The price is AED 429
AED 493 total
includes taxes & fees
6 Jul - 7 Jul
Maverick Suites at 245 Newbury St

✨Private Studio w/ Loft Center Historic Carlisle✨

✨Private Studio w/ Loft Center Historic Carlisle✨
Carlisle
9.4 out of 10, Exceptional, (34 reviews)
"Wonderful stay"
United States
Brent H.
The price is AED 533
AED 835 total
includes taxes & fees
16 Jul - 17 Jul
✨Private Studio w/ Loft Center Historic Carlisle✨

Prime Central 1brm in North End Boston

Prime Central 1brm in North End Boston
North End
9.6 out of 10, Exceptional, (25 reviews)
"Excellent location, wonderful unit! "
United States
Mary M.
The price is AED 716
AED 1,537 total
includes taxes & fees
2 Jul - 3 Jul
Prime Central 1brm in North End Boston

Beautiful 1BR near Fenway Park + Kenmore!

Beautiful 1BR near Fenway Park + Kenmore!
Fenway–Kenmore
8.0 out of 10, Very Good, (1 review)
"Although we enjoyed the property, the pics were deceiving."
United States
Barry G.
The price is AED 433
AED 1,208 total
includes taxes & fees
1 Jul - 2 Jul
Beautiful 1BR near Fenway Park + Kenmore!

Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.0 star property
Beacon Hill
7.6 out of 10, Good, (121 reviews)
"This was. A very nice, clean room. Plenty big enough for one or two people and great location, lots of dining and by the park"
United States
Rachel
The price is AED 532
AED 612 total
includes taxes & fees
30 Jun - 1 Jul
Maverick Suites at 40 Temple St

Perfect One Bedroom Stay In Downtown Boston!

Perfect One Bedroom Stay In Downtown Boston!
Downtown Boston
8.4 out of 10, Very Good, (21 reviews)
"Very easy check in, great location to walk to the ballet. Tons of great bars around"
United States
Keith
The price is AED 437
AED 863 total
includes taxes & fees
5 Jul - 6 Jul
Perfect One Bedroom Stay In Downtown Boston!

Blissful South End Studio

Blissful South End Studio
Back Bay
9.6 out of 10, Exceptional, (5 reviews)
"Great place on a quiet street convenient to everything!"
United States
Penelope D.
The price is AED 411
AED 1,094 total
includes taxes & fees
30 Jun - 1 Jul
Blissful South End Studio

Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham

Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham
Framingham
10.0 out of 10, Exceptional, (5 reviews)
"Very nice and private. Reasonably close to commuter lines into Boston."
United States
Jenny S.
The price is AED 514
AED 829 total
includes taxes & fees
30 Jun - 1 Jul
Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham

Symple Live

Symple Live
4.5 star property
Fenway–Kenmore
9.0 out of 10, Wonderful, (6 reviews)
"The property was great, aside from very busy outside streets, which made it difficult to sleep, but was not the fault of the host."
United States
Nicholas
The price is AED 529
AED 967 total
includes taxes & fees
30 Jun - 1 Jul
Symple Live

Bright 2BR by Boston Waterfront

Bright 2BR by Boston Waterfront
East Boston
9.8 out of 10, Exceptional, (33 reviews)
"Good location for our trip. Quaint and safe neighborhood. Host very responsive. "
United States
Michelle S.
The price is AED 593
AED 1,425 total
includes taxes & fees
2 Jul - 3 Jul
Bright 2BR by Boston Waterfront

Stylish Back Bay Retreat, Steps from Prudential

Stylish Back Bay Retreat, Steps from Prudential
Back Bay
9.0 out of 10, Wonderful, (12 reviews)
"Excellent location for restaurants, shops, sightseeing. Lovely buzz around the area, with park & river close by to escape if necessary. Large lounge area to put your feet up between trips, and adequate glasses etc for drinks and nibbles between the treats at the bakeries and restaurants nearby."
United Kingdom
Jude
The price is AED 489
AED 1,133 total
includes taxes & fees
1 Jul - 2 Jul
Stylish Back Bay Retreat, Steps from Prudential

Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.4 out of 10, Good, (157 reviews)
"Great location!"
United States
Kevin
The price is AED 516
AED 593 total
includes taxes & fees
30 Jun - 1 Jul
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

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?

Boston's Best Vacation Home : This vacation home rental outside of Winchester is equipped with a fireplace, air-conditioning, and laundry facilities to help you feel comfortable during your stay.

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.