Find 5 Star Hotels in Winchester, MA from AED272

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Compare Winchester 5 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

Encore Boston Harbor
View from room
Encore Boston Harbor
5.0 star property
9.6 out of 10, Exceptional, (2470)
"Enjoyed our stay. Easy access to downtown Boston utilizing resort provided transportation. Room was very comfortable. Would definitely recommend and return. "
The price is AED 1,378
AED 1,539 total
includes taxes & fees
22 Oct - 23 Oct
Encore Boston Harbor
The Langham, Boston
Pool
The Langham, Boston
5.0 star property
9.6 out of 10, Exceptional, (1003)
"Top quality hotel with the club lounge an especially nice benefit"
The price is AED 2,002
AED 2,331 total
includes taxes & fees
22 Sep - 23 Sep
The Langham, Boston
Four Seasons Hotel Boston
Lobby
Four Seasons Hotel Boston
5.0 star property
9.4 out of 10, Exceptional, (394)
"Good experience but not very quiet "
The price is AED 3,581
AED 4,170 total
includes taxes & fees
4 Oct - 5 Oct
Four Seasons Hotel Boston
Boston Harbor Hotel
Exterior
Boston Harbor Hotel
5.0 star property
9.6 out of 10, Exceptional, (1005)
"Was one of the best hotel experiences I’ve had in a long time!!"
The price is AED 3,048
AED 3,551 total
includes taxes & fees
6 Oct - 7 Oct
Boston Harbor Hotel
InterContinental Boston, an IHG Hotel
Exterior
InterContinental Boston, an IHG Hotel
5.0 star property
9.2 out of 10, Wonderful, (1001)
"Top notch property "
The price is AED 1,135
AED 1,450 total
includes taxes & fees
22 Sep - 23 Sep
InterContinental Boston, an IHG Hotel
The Newbury Boston
Front of property
The Newbury Boston
5.0 star property
9.2 out of 10, Wonderful, (310)
"Very clean. Great location. Friendly staff. Bar on the first floor could have a better menu, we weren’t impressed with food choices for lunch. Beautiful restaurant upstairs, however food was average… octopus served on the pillow of bell peppers and a ton of oil… not good."
The price is AED 2,079
AED 2,592 total
includes taxes & fees
22 Sep - 23 Sep
The Newbury Boston
The Liberty, a Marriott Luxury Collection Hotel, Boston
Exterior
The Liberty, a Marriott Luxury Collection Hotel, Boston
5.0 star property
8.6 out of 10, Excellent, (1003)
"I’ve been wanting to stay here since it was converted from the old shuttered prison. Everything about the place and staff was top notch. I’m extremely disappointed they did not disclose up front that there was construction just below my room and that Mass General with ambulances with sirens blazing all night. Stay in an upper room and city facing and it will be an amazing experience. "
The price is AED 1,465
AED 1,798 total
includes taxes & fees
22 Sep - 23 Sep
The Liberty, a Marriott Luxury Collection Hotel, Boston
The Ritz-Carlton, Boston
Lobby
The Ritz-Carlton, Boston
5.0 star property
8.8 out of 10, Excellent, (317)
"It’s close to the Boston common"
The price is AED 3,104
AED 3,614 total
includes taxes & fees
4 Oct - 5 Oct
The Ritz-Carlton, Boston
Four Seasons Hotel One Dalton Street, Boston
Exterior
Four Seasons Hotel One Dalton Street, Boston
5.0 star property
9.6 out of 10, Exceptional, (243)
"Quick and excellent service "
The price is AED 2,847
AED 3,315 total
includes taxes & fees
29 Sep - 30 Sep
Four Seasons Hotel One Dalton Street, Boston
Raffles Boston
Exterior
Raffles Boston
5.0 star property
9.6 out of 10, Exceptional, (57)
"Amazing hotel. The hotel staff were very helpful, attentive to detail and professional. The staff at the Long Bar and Terrace were a different story. We got a table in the evening and no one ever came to us, we ended up standing by the bar and just ordering a drink there. For breakfast, we placed our order and apparently we were forgotten. I had to get up and go look for a staff member. The room was great, but we found body hair in the tub as we arrived. It was taken care of but something to...
The price is AED 3,555
AED 4,140 total
includes taxes & fees
3 Oct - 4 Oct
Raffles Boston
Mandarin Oriental, Boston
Exterior
Mandarin Oriental, Boston
5.0 star property
9.4 out of 10, Exceptional, (299)
"Good place"
The price is AED 3,025
AED 3,523 total
includes taxes & fees
4 Oct - 5 Oct
Mandarin Oriental, Boston
XV Beacon
Exterior
XV Beacon
5.0 star property
9.4 out of 10, Exceptional, (354)
"The room was of of the most confortable we have been on. The only negative was the view from the window."
The price is AED 2,628
AED 3,060 total
includes taxes & fees
22 Sep - 23 Sep
XV Beacon
The Bell Inn
Exterior
The Bell Inn
5.0 star property
9.4 out of 10, Exceptional, (68)
"Lovely stay. Beautiful Inn and staff is very nice. Wish we could have stayed longer. "
The price is AED 1,731
AED 1,933 total
includes taxes & fees
28 Sep - 29 Sep
The Bell Inn
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Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Winchester.
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

450 Summer Street, Boston, MA
The price is AED272 per night from Sep 22 to Sep 23
AED272
per night
Sep 22 - Sep 23
9/10 Wonderful! (2,758 reviews)
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Frequently asked questions

What are the best 5-star hotels in Winchester?
According to Expedia guest reviews, Encore Boston Harbor, The Liberty, a Marriott Luxury Collection Hotel, Boston and XV Beacon are among the most popular 5-star hotels in Winchester. Offering best-in-class amenities and unparalleled service, you can expect an opulent and memorable stay.
How much does it cost to stay in a 5-star hotel in Winchester?
You can find various pricing options for 5-star hotels in Winchester on Expedia. The amount you pay will depend on your travel dates, length of stay and other factors. Compare all of the available accommodations for your preferred dates and make use of our pricing and other filters to score the perfect high-end stay.

  • Search for the lowest price per night from AED272

What makes a hotel 5 stars in Winchester?
Exemplary guest service is at the heart of every 5-star hotel in Winchester. From the moment you arrive, staff cater to your every need, whether recommending activities and tours or providing a nightly turn-down service. Additionally, hotels have to feature top-rate amenities to qualify for a 5-star rating. These can include luxury baths, saunas or spas, pools, gastronomic restaurants and knowledgeable concierge.
Are there any 5-star all-inclusive resorts in Winchester?
Find a luxury getaway that includes your room, meals, activities and entertainment in Winchester with our handy filters. Search for resorts rated 5 stars and click on the “All inclusive” filter. Double-check what’s included in the price. This way, you can take full advantage of all the perks on offer when you arrive.
What are the top 5-star spa hotels in Winchester?
Recharge your batteries with luxurious massages and other revitalizing treatments at Four Seasons Hotel Boston. It’s one of Winchester’s top 5-star spa properties. Mandarin Oriental Boston and Encore Boston Harbor also blend upscale accommodations with wellness programs and therapies.
Are there any 5-star vacation rentals in Winchester?
Although you won’t find any 5-star vacation rentals in Winchester on our site, we have a range of properties that promise a fantastic getaway. Discover one that matches your needs by searching our vacation rentals in Winchester.