Find Winchester 5 Star Hotels & Resorts from CA $159/night

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Check availability on Winchester 5 Star Hotels

Top Winchester 5 Star Hotels

Encore Boston Harbor
Apartment, 2 Bedrooms

Encore Boston Harbor

5.0 star property
9.6 out of 10, Exceptional, (2733)
"Check in took a little bit. Not everything was open on a Sunday before a holiday. Staff was friendly. Room was beautiful and clean "
The price is CA $369
CA $413 total
includes taxes & fees
Mar 23 - Mar 24
Encore Boston Harbor
The Langham, Boston
Exterior

The Langham, Boston

5.0 star property
9.6 out of 10, Exceptional, (1000)
"Amazing property - classy and elegant in every way. "
The price is CA $490
CA $570 total
includes taxes & fees
Feb 22 - Feb 23
The Langham, Boston
The Newbury Boston
Front of property

The Newbury Boston

5.0 star property
9.2 out of 10, Wonderful, (380)
"Great lication"
The price is CA $479
CA $632 total
includes taxes & fees
Feb 22 - Feb 23
The Newbury Boston
InterContinental Boston by IHG
View from room

InterContinental Boston by IHG

5.0 star property
9.2 out of 10, Wonderful, (998)
"Front Desk service was exceptional"
The price is CA $325
CA $436 total
includes taxes & fees
Feb 27 - Feb 28
InterContinental Boston by IHG
Boston Harbor Hotel
Suite, Multiple Beds (John Adams Presidential Suite)

Boston Harbor Hotel

5.0 star property
9.6 out of 10, Exceptional, (1004)
"Very kid friendly for an upscale hotel."
The price is CA $667
CA $778 total
includes taxes & fees
Feb 22 - Feb 23
Boston Harbor Hotel
Mandarin Oriental, Boston
Lobby

Mandarin Oriental, Boston

5.0 star property
9.4 out of 10, Exceptional, (325)
"Except for the delay in check-in, excellent. "
The price is CA $834
CA $972 total
includes taxes & fees
Mar 8 - Mar 9
Mandarin Oriental, Boston
Four Seasons Hotel Boston
Restaurant

Four Seasons Hotel Boston

5.0 star property
9.4 out of 10, Exceptional, (415)
"Beautiful property, guest rooms and facilities were lovely, staff was exceptional!"
The price is CA $979
CA $1,140 total
includes taxes & fees
Feb 21 - Feb 22
Four Seasons Hotel 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, (1005)
"A really cool atmosphere, Kasey from guest services was so wonderful and helpful and went above and beyond to make us feel welcome. The night life was great, seemed like the place to be. All staff was very good, room was clean and comfy. It was a great stay, I would Definitely go back"
The price is CA $348
CA $446 total
includes taxes & fees
Feb 27 - Feb 28
The Liberty, a Marriott Luxury Collection Hotel, 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, (279)
"Lovely! "
The price is CA $887
CA $1,033 total
includes taxes & fees
Mar 22 - Mar 23
Four Seasons Hotel One Dalton Street, Boston
XV Beacon
Exterior

XV Beacon

5.0 star property
9.4 out of 10, Exceptional, (367)
"Incredible room. Elegant design from the moment we entered the lobby. Amazing restaurant (Mooo). Complementry Lexus service is pure class. We had a wonderful stay. Thank you "
The price is CA $563
CA $655 total
includes taxes & fees
Feb 23 - Feb 24
XV Beacon
Raffles Boston
Indoor pool

Raffles Boston

5.0 star property
9.6 out of 10, Exceptional, (96)
"It’s my second time staying at a Raffles and it maintains the same level of hospitality and luxury comfort in Boston. Thank you. "
The price is CA $843
CA $982 total
includes taxes & fees
Feb 23 - Feb 24
Raffles Boston
The Ritz-Carlton, Boston
Reception

The Ritz-Carlton, Boston

5.0 star property
8.8 out of 10, Excellent, (340)
"Very nice hotel with a particular attractive gym (equinox) "
The price is CA $915
CA $1,066 total
includes taxes & fees
Feb 21 - Feb 22
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, (118)
"Property was super cute, staff were amazing. "
The price is CA $159
CA $178 total
includes taxes & fees
Feb 24 - Feb 25
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.
Seaport Hotel Boston

Seaport Hotel Boston

1 Seaport Lane, Boston, MA
The price is CA $322 per night from Mar. 7 to Mar. 8
CA $322
CA $382 total
includes taxes & fees
Mar 7 - Mar 8
9.6/10 Exceptional! (2,808 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 $205

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.