Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Apr 3 - Apr 5
In two months
May 15 - May 17
In three months
Jun 12 - Jun 14
In four months
Jul 10 - Jul 12

Our top choices for Winchester vacation rentals

1 Queen Bed with Sofa Bed (6th Floor - Elevator stops on 5th then stairs up) | Desk, iron/ironing board, free WiFi, bed sheets

Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, Good, (334 reviews)
"Very spacious"
United States
Melany
The price is ￥14,807
￥27,119 total
includes taxes & fees
Mar 17 - Mar 18
Temple Place Suites
Premium Apartment | Living area | 24-inch Smart TV with digital channels

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (29 reviews)
"This was a perfect stay. Exactly how described. Highly recommend. "
United States
Yanmarie
The price is ￥24,388
￥56,493 total
includes taxes & fees
Mar 18 - Mar 19
The Chester Hotel
Exterior

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

Free Parking at 1 Bed Basement Apt, Near BU & MIT
Fenway–Kenmore
8.0 out of 10, Very Good, (9 reviews)
"This location is so convenient to BU! Loved how easy check-in was!"
United States
Laura B.
The price is ￥15,174
￥34,821 total
includes taxes & fees
Mar 23 - Mar 24
Free Parking at 1 Bed Basement Apt, Near BU & MIT
Interior

Perfetto North End 1brm

Perfetto North End 1brm
North End
9.8 out of 10, Exceptional, (14 reviews)
"Great location- excellent place!"
United States
Deborah S.
The price is ￥21,564
￥54,534 total
includes taxes & fees
Mar 23 - Mar 24
Perfetto North End 1brm
TV

Prime Central 1brm in North End Boston

Prime Central 1brm in North End Boston
North End
9.6 out of 10, Exceptional, (25 reviews)
"Location was ideal and property was well-kept and organized. Definitely would recommend for future visits."
United States
Taye A.
The price is ￥22,841
￥55,817 total
includes taxes & fees
Mar 22 - Mar 23
Prime Central 1brm in North End Boston
Exterior

Stylish Back Bay Retreat, Steps from Prudential

Stylish Back Bay Retreat, Steps from Prudential
Back Bay
8.6 out of 10, Excellent, (7 reviews)
"Beautiful place right on historic Newbury Street. I’ll definitely return and I’d highly recommend this apartment."
United States
JEANPAUL
The price is ￥27,633
￥57,555 total
includes taxes & fees
Mar 30 - Mar 31
Stylish Back Bay Retreat, Steps from Prudential
1 bedroom, desk, iron/ironing board, WiFi

Perfect One Bedroom Stay In Downtown Boston!

Perfect One Bedroom Stay In Downtown Boston!
Downtown Boston
8.6 out of 10, Excellent, (18 reviews)
"Came to Boston to take a few college tours and this was a pretty central location. This property was also very close to several other places we were hoping to see while in town. Communication was great and check in was seamless. The property was clean and perfect for our stay. "
United States
elena d.
The price is ￥20,765
￥39,597 total
includes taxes & fees
Mar 19 - Mar 20
Perfect One Bedroom Stay In Downtown Boston!
Interior

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, (12 reviews)
"Beautiful place that made our vacation even better. There were so many hidden gems and the amenities were abundant. "
United States
Elizabeth
Bee-Themed Stay Near Boston – A Sweet and Unique Getaway
Dining

North End Entire House

North End Entire House
North End
10.0 out of 10, Exceptional, (18 reviews)
"Great location in the Northend!"
United States
Carol T.
The price is ￥31,052
￥81,415 total
includes taxes & fees
Mar 19 - Mar 20
North End Entire House
Apartment (0 Bedroom) | Interior

1 Mi to Downtown Salem: Studio w/ Fire Pit Access

1 Mi to Downtown Salem: Studio w/ Fire Pit Access
3.0 star property
Salem
9.6 out of 10, Exceptional, (5 reviews)
"Studio was very nicely laid out and the owner of the property was friendly! Area the house was in was quiet but yet still walkable to downtown Salem. Bagel place across the street was amazing as well"
United States
chris
The price is ￥21,564
￥56,278 total
includes taxes & fees
Mar 17 - Mar 18
1 Mi to Downtown Salem: Studio w/ Fire Pit Access
1 bedroom, desk, iron/ironing board, WiFi

Studio Awaits Your Next Stay!

Studio Awaits Your Next Stay!
Bay Village
9.2 out of 10, Wonderful, (5 reviews)
"Would stay again"
United States
mark p.
The price is ￥24,918
￥45,964 total
includes taxes & fees
Mar 31 - Apr 1
Studio Awaits Your Next Stay!
Property grounds

*2BR Downtown Witch House|Salem+Beverly|Hospitals

*2BR Downtown Witch House|Salem+Beverly|Hospitals
Beverly
10.0 out of 10, Exceptional, (33 reviews)
"The home was nicely renovated and comfortable and our hosts were quick to respond to questions. Check in and out was easy and we had a nice stay and will return. "
United States
Lawrence D.
The price is ￥22,043
￥53,706 total
includes taxes & fees
Mar 17 - Mar 18
*2BR Downtown Witch House|Salem+Beverly|Hospitals
Terrace/patio

Gorgeous Beacon Hills Studio next to State house

Gorgeous Beacon Hills Studio next to State house
Beacon Hill
9.8 out of 10, Exceptional, (33 reviews)
"Loved the private outdoor patio"
United States
Robin P.
The price is ￥30,045
￥58,407 total
includes taxes & fees
Mar 23 - Mar 24
Gorgeous Beacon Hills Studio next to State house
Front of property

Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.0 star property
Beacon Hill
7.6 out of 10, Good, (104 reviews)
"Great place to stay, in such a good location with everything you need nearby. Definitely recommend 😌"
United Kingdom
Jordan Elizabeth Marie
The price is ￥21,391
￥39,278 total
includes taxes & fees
Mar 22 - Mar 23
Maverick Suites at 40 Temple St
Front of property

Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (338 reviews)
"Good place"
United States
Elijah
The price is ￥17,107
￥35,272 total
includes taxes & fees
Mar 17 - Mar 18
Maverick Suites at 28 Fenway
Rooftop terrace

Marriott Vacation Club® at Custom House, Boston

Marriott Vacation Club® at Custom House, Boston
3.5 star property
Downtown Boston
9.4 out of 10, Exceptional, (623 reviews)
"Hotel is in the perfect area to go to Faneuil hall as well as to the north end everything’s in walking distance multiple restaurants you can eat high-end or very inexpensive fun time for all"
United States
Cathy
The price is ￥44,565
￥51,227 total
includes taxes & fees
Mar 22 - Mar 23
Marriott Vacation Club® at Custom House, Boston
Deluxe Double Room, Shared Bathroom | Iron/ironing board, free WiFi, bed sheets

Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.4 out of 10, (258 reviews)
"Clean room, good location, check in check out easily!"
United States
HIEN T
The price is ￥14,807
￥25,283 total
includes taxes & fees
Mar 17 - Mar 18
Premier Suites - Bay Village
Exterior detail

3BR pet-friendly Quincy house w/parking — near Adams Park

3BR pet-friendly Quincy house w/parking — near Adams Park
Quincy
9.8 out of 10, Exceptional, (47 reviews)
"very clean. comfortable beds. Very nice stay."
Germany
Stefanie K.
The price is ￥23,081
￥53,973 total
includes taxes & fees
Mar 22 - Mar 23
3BR pet-friendly Quincy house w/parking — near Adams Park
Interior

1880 updated Victorian 1st floor, water views

1880 updated Victorian 1st floor, water views
Salem
10.0 out of 10, Exceptional, (5 reviews)
"This house is absolutely beautiful, perfect location for all the convince of down town and the host was a sweetheart! "
United States
Shelby L.
The price is ￥28,751
￥36,753 total
includes taxes & fees
Mar 17 - Mar 18
1880 updated Victorian 1st floor, water views
1 bedroom, travel crib, free WiFi, bed sheets

Re-listed: Adorable Condo Beverly - Salem - Halloween

Re-listed: Adorable Condo Beverly - Salem - Halloween
Beverly
9.8 out of 10, Exceptional, (19 reviews)
"Space was clean with a personal touch for our stay. Matty made some great suggestions in and around Beverly/ Salem/ Boston. We loved the effort to make the stay feel welcoming."
United States
Miles G.
The price is ￥14,943
￥39,529 total
includes taxes & fees
Mar 17 - Mar 18
Re-listed: Adorable Condo Beverly - Salem - Halloween
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

Omni Parker House

Omni Parker House

10/10 Excellent
"Main entrance was a bit tight to pass through with my wide suitcase. Also there are steps making it more difficult. I suggest using the side entrance. The store attached to hotel was great. Picked up coffee and snacks. A bit pricey but I guess you’re paying for convenience. My room was clean. Surprised that after taking an elevator to my floor I still had to take more steps up to get to my room. So be aware if your like me and struggle with steps. I wonder if it’s because I stayed in the smaller room. The room is snug like stretchy jeans. Five more pounds and I wouldn’t have fit. Worked out well for me since I don’t need a lot of room. Most important it was clean and smelled clean. Housekeeping was great. They were able to give me a mini fridge which I really appreciated. "
Patria A 4-night trip
Posted 2 hours ago
Omni Parker House

Find out more about Winchester

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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.

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

Spacious, New Renovation | Near T: This vacation home rental outside of Winchester is equipped with a barbecue grill, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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.