Find Winchester 5 Star Hotels & Resorts from CA $161/night

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Top Winchester 5 Star Hotels

Encore Boston Harbor
Apartment, 2 Bedrooms

Encore Boston Harbor

5.0 star property
9.6 out of 10, Exceptional, (2613)
"The rooms are beautiful with all new technology and awesome bathrooms. "
The price is CA $328
CA $366 total
includes taxes & fees
Jan 26 - Jan 27
Encore Boston Harbor
The Langham, Boston
Exterior

The Langham, Boston

5.0 star property
9.6 out of 10, Exceptional, (1007)
"Nice comfortable location and hotel experience"
The price is CA $461
CA $537 total
includes taxes & fees
Jan 9 - Jan 10
The Langham, Boston
InterContinental Boston, an IHG Hotel
View from room

InterContinental Boston, an IHG Hotel

5.0 star property
9.2 out of 10, Wonderful, (1013)
"My stay was amazing and the staff was exceptional "
The price is CA $316
CA $419 total
includes taxes & fees
Feb 2 - Feb 3
InterContinental Boston, an IHG Hotel
Boston Harbor Hotel
Suite, Multiple Beds (John Adams Presidential Suite)

Boston Harbor Hotel

5.0 star property
9.6 out of 10, Exceptional, (1008)
"I vacation all over usa from keywest,Miami,Orlando,New York. The service you get from Boston Harbor hotel is unmatched! 5 star hotel with 5 star Service from beginning til the end. The employees there are happy & always ready to assist you making you feel welcomed like at home. We stayed for New Year’s Eve it was lovely. "
The price is CA $627
CA $731 total
includes taxes & fees
Jan 6 - Jan 7
Boston Harbor Hotel
Four Seasons Hotel Boston
Restaurant

Four Seasons Hotel Boston

5.0 star property
9.4 out of 10, Exceptional, (409)
"Beautiful hotel "
The price is CA $997
CA $1,161 total
includes taxes & fees
Jan 8 - Jan 9
Four Seasons Hotel Boston
The Newbury Boston
Front of property

The Newbury Boston

5.0 star property
9.2 out of 10, Wonderful, (358)
"Staff is amazing. Best hotel I ever stayed at. Looking forward to spending NYE every year at the new berry!"
The price is CA $525
CA $687 total
includes taxes & fees
Jan 7 - Jan 8
The Newbury Boston
The Liberty, a Marriott Luxury Collection Hotel, Boston
Property amenity

The Liberty, a Marriott Luxury Collection Hotel, Boston

5.0 star property
8.6 out of 10, Excellent, (1006)
"We had a wonderful stay!"
The price is CA $397
CA $498 total
includes taxes & fees
Feb 1 - Feb 2
The Liberty, a Marriott Luxury Collection Hotel, Boston
Mandarin Oriental, Boston
Lobby

Mandarin Oriental, Boston

5.0 star property
9.4 out of 10, Exceptional, (320)
"The service is simply amazing. Highly recommended. "
The price is CA $655
CA $763 total
includes taxes & fees
Jan 11 - Jan 12
Mandarin Oriental, Boston
Four Seasons Hotel One Dalton Street, Boston
Indoor pool, open 6:00 AM to 9:00 PM, sun loungers

Four Seasons Hotel One Dalton Street, Boston

5.0 star property
9.6 out of 10, Exceptional, (276)
"The stay was amazing, the facilities were great and the staff were courteous. "
The price is CA $852
CA $993 total
includes taxes & fees
Jan 19 - Jan 20
Four Seasons Hotel One Dalton Street, Boston
Raffles Boston
Indoor pool

Raffles Boston

5.0 star property
9.6 out of 10, Exceptional, (85)
"Excellent services. "
The price is CA $809
CA $942 total
includes taxes & fees
Jan 7 - Jan 8
Raffles Boston
XV Beacon
Exterior

XV Beacon

5.0 star property
9.4 out of 10, Exceptional, (360)
"Staff was extremely helpful "
The price is CA $644
CA $749 total
includes taxes & fees
Jan 6 - Jan 7
XV Beacon
The Ritz-Carlton, Boston
City view

The Ritz-Carlton, Boston

5.0 star property
8.8 out of 10, Excellent, (335)
"Staff was attentive and quick to respond. "
The price is CA $831
CA $967 total
includes taxes & fees
Jan 10 - Jan 11
The Ritz-Carlton, Boston
The Bell Inn
Honeymoon Room | In-room dining

The Bell Inn

5.0 star property
9.4 out of 10, Exceptional, (102)
"Great job on the rehab of the building. "
The price is CA $270
CA $302 total
includes taxes & fees
Jan 6 - Jan 7
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.
Hilton Boston Park Plaza

Hilton Boston Park Plaza

50 Park Plaza, Boston, MA
The price is CA $161 per night from Jan. 16 to Jan. 17
CA $161
CA $246 total
includes taxes & fees
Jan 16 - Jan 17
8.2/10 Very Good! (3,280 reviews)
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Frequently asked questions

What are the best 5-star hotels in Winchester?
Get set for 5-star indulgence at Encore Boston Harbor, The Liberty, a Marriott Luxury Collection Hotel, Boston or XV Beacon. These are among the top-rated escapes in Winchester according to Expedia traveler reviews. Pick one and get a taste of the good life!
How much does it cost to stay in a 5-star hotel in Winchester?
The amount you pay for a 5-star hotel in Winchester depends on things like when you plan to go and the length of your trip. Our top tip for scoring the best deal? Use our pricing filters to check out the available hotels for your preferred dates.

  • Search for the lowest price per night from CA $161

What makes a hotel 5 stars in Winchester?
Flawless guest service is the defining feature of every 5-star hotel in Winchester. From the second you arrive, staff attend to your every need, whether offering luggage assistance and storage or providing in-room beauty treatments. What’s more, hotels have to feature upscale amenities to meet the standard for a 5-star rating. These can include luxury bathrooms, saunas or spas, pools, gastronomic restaurants and knowledgeable concierge.
Are there any 5-star all-inclusive resorts in Winchester?
Our filters are the best way to narrow down what you’re looking for. Select “All inclusive” and “5-star” to show the most luxurious properties in Winchester where your lodging, meals, activities and entertainment are included in the price. At these escapes, your vacation is pure extravagance from the moment you pull up to the entrance.
What are the top 5-star spa hotels in Winchester?
Pamper yourself with a spa vacation at Four Seasons Hotel Boston and let your cares drift away. Mandarin Oriental, Boston and Encore Boston Harbor are other 5-star options in Winchester where you can experience the rejuvenating and soothing powers of wellness programs and spa treatments.
Are there any 5-star vacation rentals in Winchester?
You won’t find any 5-star vacation rentals in Winchester on our site, but there are a range of other highly rated properties worth checking out. Scan through our vacation rentals in Winchester to find the ideal place for your getaway.