Find 5 Star Hotels in Winchester, MA from AED232

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

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, (2477)
"Fitness center and access to casino was great"
The price is AED 1,127
AED 1,259 total
includes taxes & fees
27 Oct - 28 Oct
Encore Boston Harbor
The Langham, Boston
Pool
The Langham, Boston
5.0 star property
9.6 out of 10, Exceptional, (1001)
"Top quality hotel with the club lounge an especially nice benefit"
The price is AED 1,965
AED 2,288 total
includes taxes & fees
29 Sep - 30 Sep
The Langham, Boston
Four Seasons Hotel Boston
Lobby
Four Seasons Hotel Boston
5.0 star property
9.2 out of 10, Wonderful, (396)
"Good experience but not very quiet "
The price is AED 3,581
AED 4,170 total
includes taxes & fees
29 Sep - 30 Sep
Four Seasons Hotel Boston
The Newbury Boston
Front of property
The Newbury Boston
5.0 star property
9.2 out of 10, Wonderful, (311)
"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 2,526
AED 3,112 total
includes taxes & fees
2 Oct - 3 Oct
The Newbury Boston
Boston Harbor Hotel
Exterior
Boston Harbor Hotel
5.0 star property
9.6 out of 10, Exceptional, (1003)
"It was outstanding in every way! "
The price is AED 2,652
AED 3,090 total
includes taxes & fees
27 Oct - 28 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, (1002)
"We had a wonderful stay it was close to a lot of things and staff was amazing "
The price is AED 1,631
AED 2,028 total
includes taxes & fees
29 Sep - 30 Sep
InterContinental Boston, an IHG Hotel
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 1,296
AED 1,601 total
includes taxes & fees
13 Oct - 14 Oct
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
29 Sep - 30 Sep
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, (245)
"Incredible hotel and staff. First class experience!"
The price is AED 3,030
AED 3,529 total
includes taxes & fees
6 Oct - 7 Oct
Four Seasons Hotel One Dalton Street, Boston
Mandarin Oriental, Boston
Exterior
Mandarin Oriental, Boston
5.0 star property
9.4 out of 10, Exceptional, (301)
"The room we initially booked did not match the images presented on the website, leading to disappointment during our three-night stay in an accessible room. The shower depicted in the photos was quite different from what we encountered, and the beds were significantly smaller than anticipated. Although we raised these concerns with the hotel, we were unable to switch rooms until our third night. This was particularly disheartening as we had been looking forward to this long-awaited break. When...
The price is AED 3,155
AED 3,674 total
includes taxes & fees
6 Oct - 7 Oct
Mandarin Oriental, Boston
Raffles Boston
Exterior
Raffles Boston
5.0 star property
9.6 out of 10, Exceptional, (59)
"Limited breakfast menu."
The price is AED 3,291
AED 3,832 total
includes taxes & fees
2 Oct - 3 Oct
Raffles Boston
XV Beacon
Exterior
XV Beacon
5.0 star property
9.4 out of 10, Exceptional, (355)
"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
29 Sep - 30 Sep
XV Beacon
The Bell Inn
Exterior
The Bell Inn
5.0 star property
9.4 out of 10, Exceptional, (71)
"I would say this comes close to being one of my favorite hotel stays ever. The room was clean, modern, welcoming, and cozy. The amenities were great- the breakfast provided in the morning by the coffee bar was awesome! Staff was extremely friendly. The whole building itself was very charming. I have already recommended to friends and family who are thinking of visiting this area. It was a quick drive to Salem. I loved it here. Thank you for a fantastic stay!"
The price is AED 1,731
AED 1,933 total
includes taxes & fees
29 Sep - 30 Sep
The Bell Inn
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Winchester.
Hilton Boston Park Plaza

Hilton Boston Park Plaza

50 Park Plaza, Boston, MA
The price is AED232 per night from Sep 29 to Sep 30
AED232
per night
Sep 29 - Sep 30
8.2/10 Very Good! (3,315 reviews)
Still don't see what you're looking for?
See all properties in Winchester.
You can also use these popular filters to refine your search.
PoolSpaHot tubBreakfast includedWaterpark
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.

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 AED232

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.