Winchester Vacation Rentals

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Oct 24 - Oct 25
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Oct 25 - Oct 26
This weekend
Oct 24 - Oct 26
Next weekend
Oct 31 - Nov 2

Vacation Rentals in Winchester

42-inch TV with satellite channels
Maverick Suites at 400 Columbus Ave
Maverick Suites at 400 Columbus Ave
2.0 star property
7.2 out of 10, Good, (126)
"I thoroughly enjoyed my stay. Great property in a nice neighborhood in Back Bay. Bonus: it's also near the Logan Express bus stop for easy airport access. "
United States
Mark
The price is ￥14,008
￥30,135 total
includes taxes & fees
Nov 18 - Nov 19
Maverick Suites at 400 Columbus Ave
Front of property
Maverick Suites at 40 Temple St
Maverick Suites at 40 Temple St
2.0 star property
7.4 out of 10, Good, (100)
"Great location "
Canada
James
The price is ￥20,143
￥37,123 total
includes taxes & fees
Nov 19 - Nov 20
Maverick Suites at 40 Temple St
Desk, laptop workspace, free WiFi, bed sheets
Bay Village Suites
Bay Village Suites
2.0 star property
6.4 out of 10, (235)
"Great location nice neighborhood "
United States
Jose
Bay Village Suites
Lobby lounge
Global Luxury Suites Downtown Boston
Global Luxury Suites Downtown Boston
4.0 star property
8.0 out of 10, Very Good, (614)
"This unit and location was perfect for my trip! Super close to many of the attractions that we wanted to visit. "
United States
Lily
Global Luxury Suites Downtown Boston
Exterior
Maverick Suites at 245 Newbury St
Maverick Suites at 245 Newbury St
2.0 star property
8.2 out of 10, Very Good, (150)
"Clean. Bed super comfortable, easy walk to Fenway, restaurants, subway, shops, library"
United States
Elizabeth rising
The price is ￥21,564
￥38,757 total
includes taxes & fees
Nov 19 - Nov 20
Maverick Suites at 245 Newbury St
Individually furnished, laptop workspace, iron/ironing board, bed sheets
No. 284 Back Bay Hotel, Sonder by Marriott Bonvoy
No. 284 Back Bay Hotel, Sonder by Marriott Bonvoy
4.0 star property
9.2 out of 10, Wonderful, (944)
"The property was awesome, well located, not far to jump on trains etc Close to MGM musical hall, which was the reason for our trip. Would 100% recommend this property if your looking for a nice peaceful area but close enough to all the popular touristy areas. Loved our stay, thank you "
United Kingdom
Lyndsey
The price is ￥25,956
￥30,615 total
includes taxes & fees
Nov 9 - Nov 10
No. 284 Back Bay Hotel, Sonder by Marriott Bonvoy
Deluxe Studio | 1 bedroom, desk, iron/ironing board, free WiFi
Temple Place Suites
Temple Place Suites
2.5 star property
7.0 out of 10, Good, (298)
"Very convenient place to stay, near transportation and waking distance to historic points and shopping. "
United States
Carolina
The price is ￥14,492
￥26,263 total
includes taxes & fees
Nov 13 - Nov 14
Temple Place Suites
Iron/ironing board, free WiFi, bed sheets
Premier Suites - Bay Village
Premier Suites - Bay Village
2.0 star property
6.4 out of 10, (237)
"Clean room, good location, check in check out easily!"
United States
HIEN T
The price is ￥30,213
￥42,622 total
includes taxes & fees
Oct 26 - Oct 27
Premier Suites - Bay Village
Deluxe Studio Suite (2nd Floor - Unit 202) | 1 bedroom, individually furnished, iron/ironing board, free WiFi
Maverick Suites at 28 Fenway
Maverick Suites at 28 Fenway
3.0 star property
8.8 out of 10, Excellent, (303)
"great location"
United States
Mario
The price is ￥14,786
￥31,905 total
includes taxes & fees
Nov 18 - Nov 19
Maverick Suites at 28 Fenway
Apartment, 2 Bedrooms | Private kitchen | Mini-fridge, microwave, cookware/dishes/utensils, paper towels
Maverick Suites at 402 Columbus Ave
Maverick Suites at 402 Columbus Ave
2.5 star property
8.0 out of 10, Very Good, (65)
"Loved how cozy and clean it was. Location was great, near many points of interest. Parking at an extra fee, but plenty of street parking in the area. "
United States
Isaiah Joel Santa
The price is ￥16,083
￥32,520 total
includes taxes & fees
Nov 23 - Nov 24
Maverick Suites at 402 Columbus Ave
Interior entrance
Maverick Suites at 89 Marion
Maverick Suites at 89 Marion
2.0 star property
8.4 out of 10, Very Good, (261)
"Had an amazing time. Loved the property and it's location in proximity to entertainment, transportation, dining and scenic entertainment. "
United States
Nicole
The price is ￥17,380
￥33,049 total
includes taxes & fees
Nov 23 - Nov 24
Maverick Suites at 89 Marion
Property grounds
Crescent Suites Hotel
Crescent Suites Hotel
3.0 star property
9.6 out of 10, Exceptional, (1114)
"The staff were friendly and the accommodation was good"
United States
Sudha
Crescent Suites Hotel
Exterior
Best Location Studio In Downtown Boston
Best Location Studio In Downtown Boston
10.0 out of 10, Exceptional, (1)
"In town to celebrate a special event."
United States
Pam P.
The price is ￥21,115
￥38,580 total
includes taxes & fees
Nov 19 - Nov 20
Best Location Studio In Downtown Boston
Luxury Suite 2 | Living area | Smart TV, Netflix, Hulu, streaming services
The Monty Boston
The Monty Boston
2.5 star property
9.4 out of 10, Exceptional, (25)
"Thos was agreat place to stay for my family. It is very spacious."
United States
David
The price is ￥91,441
￥131,423 total
includes taxes & fees
Oct 31 - Nov 1
The Monty Boston
Apartment | 1 bedroom, premium bedding, desk, iron/ironing board
Charlesgate Suites
Charlesgate Suites
3.5 star property
9.4 out of 10, Exceptional, (194)
"New spot for us in South Bay. Convenient and easy with easy walk to Commonwealth and restaurants of Newbury"
United States
Brian
The price is ￥31,739
￥62,796 total
includes taxes & fees
Nov 10 - Nov 11
Charlesgate Suites
View from property
Sonder by Marriott Bonvoy The Magnolia Apartments Back Bay
Sonder by Marriott Bonvoy The Magnolia Apartments Back Bay
3.5 star property
8.8 out of 10, Excellent, (77)
"Excellent location in the heart of shops. Quiet and clean location. Highly recommend and would definitely stay again ❤️."
United States
Michelle
The price is ￥38,965
￥45,960 total
includes taxes & fees
Nov 13 - Nov 14
Sonder by Marriott Bonvoy The Magnolia Apartments Back Bay
City Studio | 1 bedroom, Egyptian cotton sheets, premium bedding, memory foam beds
The Chester Hotel
The Chester Hotel
4.0 star property
8.4 out of 10, Very Good, (25)
"The property was spacious and clean. We enjoyed our stay!"
United States
Bryan
The price is ￥27,070
￥58,183 total
includes taxes & fees
Nov 19 - Nov 20
The Chester Hotel
Marina
♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥
♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥
10.0 out of 10, Exceptional, (68)
"I was beyond impressed with my stay here in Marblehead! As a solo traveler, I felt safe in this Vrbo property. Everything was beyond clean, access was easy, and having a dedicated parking spot was amazing. It was the perfect place to stay!"
United States
Keeley H.
The price is ￥17,464
￥43,198 total
includes taxes & fees
Nov 12 - Nov 13
♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥
Apartment | 1 bedroom, desk, laptop workspace, free WiFi
Furnished Apartments near Encore Boston
Furnished Apartments near Encore Boston
2.5 star property
8.4 out of 10, Very Good, (6)
"Great place. Very clean. Great communication."
United States
Michele
The price is ￥37,690
￥59,145 total
includes taxes & fees
Oct 26 - Oct 27
Furnished Apartments near Encore Boston
Interior
Ideal North End 1brm Central To Everything
Ideal North End 1brm Central To Everything
9.6 out of 10, Exceptional, (36)
"We had a very nice stay. Such a great location! Walkable to tons of restaurants and right near the Paul Revere statue and Old North Church!"
United States
Sean R.
The price is ￥22,126
￥54,200 total
includes taxes & fees
Nov 17 - Nov 18
Ideal North End 1brm Central To Everything
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

Harborside Inn Of Boston

Harborside Inn Of Boston

10/10 Excellent
"Clean room and nice area"
Andrew 3-night trip
Posted 10 hours ago
Harborside Inn Of Boston

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?

Casa Castor • Private Room 1: This vacation home rental outside of Winchester has air-conditioning and free WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge to make your meal-planning easier.

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.