Winchester Holiday Rentals - Holiday Homes in Winchester

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Vacation Rentals in Winchester

"Good clean and spacious. Well appointed apartment. Only negative was lack of qater pressure"

P16,864 total

includes taxes & fees

Dec 8 - Dec 9

"Great stay. "

P11,197 total

includes taxes & fees

Dec 28 - Dec 29

"It was great. Very clean and especially loved the heating fan in the bathroom. The only thing I’d recommend to enhance the experience would be a more comfortable sofa bed. "

P11,077 total

includes taxes & fees

Dec 2 - Dec 3

Desk, iron/ironing board, free WiFi, bed sheets

"It would be pretty hard to beat the convenience of this location. You can walk to pretty much anywhere in Boston from here. Subways were close, there's plenty of places to eat right near by. The communication from the property management was excellent. Expect this place to be... quirky. It's definitely run down. The elevator was an adventure, though it always ran. The water pressure is lacking. The floor was very squeaky. Our room was very dark. And the bed was not particularly comfortable. But...

P10,087 total

includes taxes & fees

Dec 18 - Dec 19

Desk, laptop workspace, free WiFi, bed sheets

"My stay at the Bay Village Hotel in Boston was amazing. To be honest, it was my first experience staying in a self-serving hotel like this. However, everything was good. No one disturbed me, and every time, the hotel was quiet like I was alone in the entire building, and it was convenient. "

"Perfect location!"

P8,441 total

includes taxes & fees

Dec 22 - Dec 23

"Fourth floor walk up, nice place. No front desk, all access information provided ahead of time. "

P11,588 total

includes taxes & fees

Dec 28 - Dec 29

"The place is clean and functional. The kitchen area is equipped with a fridge (no freezer), a microwave oven, a coffee maker (with coffee pods provided for the number of days of stay), dish detergent and sponge for washing up. There are mugs, bowls, dishes and silverware in the cupboard. The bathroom is clean, with clean towels, shampoo and soap. The walls and floors are a bit thin and there can be some noise from neighbors, but not a lot. Self check-in is easy, with access codes sent the day...

P9,595 total

includes taxes & fees

Nov 30 - Dec 1

"Nice property, good sized and well furnished."

P10,239 total

includes taxes & fees

Dec 23 - Dec 24

Iron/ironing board, free WiFi, bed sheets

"Great location, great communication. Perfect place to stay if you just need a place to sleep close to the train station. Expect it to be… rustic. Bring shower shoes for the shared bathroom. The bed was super comfortable. It’s a tiny space, but has everything you need if you’re not going to be in the room much. Overall, good experience. Just don’t go into it expecting the space to be perfect."

"Beacon Hill is a good central location and about 30 minutes walk to the Convention Center. There’s a Whole Foods nearby for groceries. My room was small but fine for one person. Check in and out was easy. My only complaint was that there was no way to adjust the fan speed on the climate control and it was noidy but this was not a dealbreaker. "

P11,224 total

includes taxes & fees

Dec 28 - Dec 29

"This is an entire apartment near the airport. There is public transportation nearby. The apartment was nice and clean. The front desk is not always there. There are several building and several entrances which make it a little confusing. Was dropped off at one side entrance, walked to the front, then the front desk person walked me to another building into the back entrance. But when I left I left out of the front entrance. So yeah, that was very confusing. Otherwise my stay was pleasant "

P15,475 total

includes taxes & fees

Dec 11 - Dec 12

42-inch flat-screen TV with digital channels, TV, streaming services

"Fantastic, Pierce-Sonder is always our first choice while visiting Boston. We come often for treatment at Dana Farber Cancer Institute. "

P11,686 total

includes taxes & fees

Dec 19 - Dec 20

"Having to have cleaning of the room as an extra charge should be noted clearly for any future occupants. The unit is not close to any restaurant or store unless you want to walk 10 minutes to get there and carry anything back. It is not convenient to anything of note. Would not stay there again. It was clean but that's the best I could say for the property. "

P10,495 total

includes taxes & fees

Dec 28 - Dec 29

"Easy transaction and super convenient"

P11,224 total

includes taxes & fees

Dec 28 - Dec 29

1 bedroom, individually decorated, individually furnished

"Sensational location "

P12,551 total

includes taxes & fees

Dec 24 - Dec 25

Premium bedding, desk, iron/ironing board, free WiFi

"Great space, great location. Just as advertised. Oct 2024 EVERYTHING looked new…floors, appliances, paint, furniture. Everything. Everything worked well ( though the fireplace would only stay lit for 5 minutes. Exactly FIVE). Communication was awesome. Prompt and helpful. Only criticism: did not know that there was NO ELEVATOR until the day of check in. At 61 with bad knees and four bags, getting settled in was a major hassle. Four narrow flights of winding stairs. Other than...

Individually furnished, iron/ironing board, free cribs/infant beds

"Nestled in the Government sector of town. Beautiful historical buildings and streets. Easy walk to most everywhere. "

P12,744 total

includes taxes & fees

Dec 12 - Dec 13

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"Easy to get to from the airport - free bus takes you directly across the street. If you are looking to explore the historic side of Boston this will be a bit out of the way but still accessible by public transit."

P11,294 total

includes taxes & fees

Dec 20 - Dec 21

"Concierge was incredibly friendly and helpful"

P10,544 total

includes taxes & fees

Dec 27 - Dec 28

"Easy check in and check out. "

P13,609 total

includes taxes & fees

Dec 1 - Dec 2

Find out more about Winchester

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Recent reviews of Winchester properties

Club Quarters Hotel Faneuil Hall, Boston

5/5 Excellent

"The hotel is in a super central location, walking distance to so many sights and the train. The hotel also looked very nice and the room/bathroom was super clean. I would definitely recommend this hotel to anyone visiting Boston!"

A verified traveler stayed at Club Quarters Hotel Faneuil Hall, Boston

Posted 15 hours ago

5/5 Excellent

"Unexpected gem! Despite the smaller room size, there is everything you could possibly need. The staff is very friendly and helpful as well. Buffet breakfast is yum and convenient. The location is perfect for walking and being a tourist or for going to the games) concerts and getting some rest. Well done! Looking forward to exploring other CitizenM stays.. NYC and Miami are next"

A verified traveler from Winter Garden stayed at citizenM Boston North Station

Posted 20 hours ago

5/5 Excellent

"I had a pleasant time staying at this Hotel even if it was only for a limited amount of time. The room was clean and comfortable. I love the layout of having the bathroom vanity on the other side and the lighting was fantastic. Would absolutely stay at here again."

A verified traveler stayed at Omni Boston Hotel at the Seaport

Posted 2 days ago

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 can I see and do in Winchester?

Family-friendly attractions include Winter Pond, whereas Middlesex Fells Reservation is a spot to enjoy the outdoors. 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.

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Winchester Vacation Rentals

Check Winchester vacation rental availability

Vacation Rentals in Winchester

Global Luxury Suites Downtown Boston

Maverick Suites at 28 Fenway

Crescent Suites Hotel

Temple Place Suites

Bay Village Suites

Sonder 907 Main

Maverick Suites at 245 Newbury St

Maverick Suites at 89 Marion

No. 284 powered by Sonder

Premier Suites - Bay Village

Maverick Suites at 40 Temple St

Global Luxury Suites East Boston

Sonder at Pierce Boston

Maverick Suites at 400 Columbus Ave

Maverick Suites at 402 Columbus Ave

Sonder The Magnolia

Charlesgate Suites

Sonder The Hancock

Other types of properties in Winchester you may be interested in

Seaport Hotel Boston

Hilton Boston Park Plaza

Omni Parker House

Find out more about Winchester

Recent reviews of Winchester properties

Club Quarters Hotel Faneuil Hall, Boston

Harborside Inn Of Boston

Hampton Inn Boston - Logan Airport

citizenM Boston North Station

Four Points by Sheraton Boston Newton

The Dagny Boston

Omni Boston Hotel at the Seaport

Omni Parker House

Seaport Hotel Boston

Frequently asked questions