A town with a prominent church, a large building with a clock tower, and a mix of residential and commercial buildings surrounded by greenery.

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Check availability on Winchester 5 Star Hotels

Our top choices for Winchester 5-star hotels

Breakfast, lunch and brunch served

The Langham, Boston

The Langham, Boston
5.0 star property
Downtown Boston
9.6 out of 10, Exceptional, (1,007 reviews)
"Todo excelente!!"
Mexico
Eduardo
The price is 11.738.220 ₫
13.669.157 ₫ total
includes taxes & fees
14 Aug - 15 Aug
The Langham, Boston
4 restaurants; breakfast, lunch and dinner served

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport
5.0 star property
Seaport District
9.2 out of 10, Wonderful, (4,834 reviews)
"Great location and rooms"
United States
Aimee
The price is 6.176.352 ₫
8.262.972 ₫ total
includes taxes & fees
31 Jul - 1 Aug
Omni Boston Hotel at the Seaport
Apartment, 2 Bedrooms | Premium bedding, down duvets, pillow-top beds, minibar

Encore Boston Harbor

Encore Boston Harbor
5.0 star property
Everett
9.6 out of 10, Exceptional, (3,958 reviews)
"It was an incredible place to stay, can’t wait to go back!"
United States
Patricia
The price is 7.149.236 ₫
7.985.696 ₫ total
includes taxes & fees
12 Aug - 13 Aug
Encore Boston Harbor
3 restaurants; breakfast, lunch, dinner and brunch served

The Charles Hotel

The Charles Hotel
5.0 star property
West Cambridge
9.4 out of 10, Exceptional, (1,000 reviews)
"Great location"
United States
Carmen
The price is 9.328.449 ₫
10.816.336 ₫ total
includes taxes & fees
13 Aug - 14 Aug
The Charles Hotel
Suite, Multiple Beds (John Adams Presidential Suite) | Frette Italian sheets, premium bedding, pillow-top beds, minibar

Boston Harbor Hotel

Boston Harbor Hotel
5.0 star property
North End
9.8 out of 10, Exceptional, (1,016 reviews)
"Couldn’t ask for a better place to stay while in Boston."
United States
Beverly
The price is 13.624.550 ₫
15.880.229 ₫ total
includes taxes & fees
2 Aug - 3 Aug
Boston Harbor Hotel
Lunch and dinner served

The Newbury Boston

The Newbury Boston
5.0 star property
Back Bay
9.4 out of 10, Exceptional, (685 reviews)
"Great location, staff and service."
United States
Gino
The price is 14.439.988 ₫
18.191.128 ₫ total
includes taxes & fees
9 Aug - 10 Aug
The Newbury Boston
Property amenity

The Liberty, a Marriott Luxury Collection Hotel, Boston

The Liberty, a Marriott Luxury Collection Hotel, Boston
5.0 star property
West End
8.8 out of 10, Excellent, (1,000 reviews)
The price is 7.775.586 ₫
9.819.098 ₫ total
includes taxes & fees
26 Jul - 27 Jul
The Liberty, a Marriott Luxury Collection Hotel, Boston
Exterior

InterContinental Boston by IHG

InterContinental Boston by IHG
5.0 star property
Downtown Boston
9.4 out of 10, Exceptional, (1,145 reviews)
"Lovely property and lovely staff. Excellent location for the harbor."
United States
Maxine
The price is 6.444.552 ₫
8.696.968 ₫ total
includes taxes & fees
2 Aug - 3 Aug
InterContinental Boston by IHG
Breakfast, lunch and dinner served

Mandarin Oriental, Boston

Mandarin Oriental, Boston
5.0 star property
Back Bay
9.4 out of 10, Exceptional, (434 reviews)
"The staff were aware of our celebration and helped us accomplish our goals in celebrating. They were kind and thoughtful. Everything was lovely, the decor, the furniture, the space, the amenities."
United States
Christina
The price is 14.702.800 ₫
17.121.410 ₫ total
includes taxes & fees
2 Aug - 3 Aug
Mandarin Oriental, Boston
Terrace/patio

Four Seasons Hotel Boston

Four Seasons Hotel Boston
5.0 star property
Bay Village
9.4 out of 10, Exceptional, (474 reviews)
"The best hotel in Boston "
United States
Madina
The price is 21.266.550 ₫
24.764.899 ₫ total
includes taxes & fees
2 Aug - 3 Aug
Four Seasons Hotel Boston
Reception

The Ritz-Carlton, Boston

The Ritz-Carlton, Boston
5.0 star property
Downtown Boston
9.0 out of 10, Wonderful, (472 reviews)
"Great hotel, great food and friendly staff "
United States
Oswaldo
The price is 16.514.395 ₫
19.231.262 ₫ total
includes taxes & fees
2 Aug - 3 Aug
The Ritz-Carlton, Boston
Indoor pool

Raffles Boston

Raffles Boston
5.0 star property
Back Bay
9.6 out of 10, Exceptional, (280 reviews)
"This hotel was so beautiful and exceptional "
United States
Darlene
The price is 17.118.260 ₫
19.934.213 ₫ total
includes taxes & fees
9 Aug - 10 Aug
Raffles Boston
Exterior

XV Beacon

XV Beacon
5.0 star property
Beacon Hill
9.4 out of 10, Exceptional, (395 reviews)
"The location was fantastic for all things Boston! It was a very walkable location and such a comfortable room and a very friendly staff that was very helpful."
United States
Robin
The price is 14.059.552 ₫
16.372.350 ₫ total
includes taxes & fees
9 Aug - 10 Aug
XV Beacon
Honeymoon Room | In-room dining

The Bell Inn

The Bell Inn
5.0 star property
Peabody
9.4 out of 10, Exceptional, (260 reviews)
"Awesome place to stay!!"
United States
Joseph A
The price is 3.979.148 ₫
4.444.708 ₫ total
includes taxes & fees
28 Jul - 29 Jul
The Bell Inn
Lounge

Luxury Apartments by Hyatus Boston Somerville

Luxury Apartments by Hyatus Boston Somerville
5.0 star property
Inner Belt
10.0 out of 10, Exceptional, (3 reviews)
"I was staying in the Boston area for work and this was the perfect place to stay. Lots of room and easy to get to and the staff were very responsive and helpful. I would highly recommend!"
Canada
Peter
Luxury Apartments by Hyatus Boston Somerville
Billiards

Luxury Apartments by Hyatus at Boston Everett

Luxury Apartments by Hyatus at Boston Everett
5.0 star property
Everett
9.2 out of 10, Wonderful, (5 reviews)
"Family trip for competition travel and the property was exactly what we needed. Clean room, comfortable beds, and a peaceful environment after long tournament days. Staff was professional and welcoming, and the location made everything easier for our family. Traveling with kids can be stressful, but this stay helped us reset and stay focused. Would definitely stay again. "
United States
Trenthony
Luxury Apartments by Hyatus at Boston Everett
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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 5.225.740 ₫ per night from 26 Jul to 27 Jul
5.225.740 ₫
6.981.102 ₫ total
26 Jul - 27 Jul
includes taxes & fees
9.6/10 Exceptional! (4,590 reviews)
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Learn more about Winchester

Stroll along the shores of Mystic Lake, where locals gather for picnics and kayaking on sunny afternoons. History buffs can explore the Wright-Locke Farm, learning about sustainable agriculture while kids enjoy the farm animals and nature trails.

See all hotels in Winchester
A historic building with a clock tower, red brick walls, and a green roof.

Top Winchester Hotel Reviews

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

8/10 Good
"Always a great day at Omni seaport!"
Samantha 1-night trip
Posted 4 hours ago
Omni Boston Hotel at the Seaport

Frequently asked questions

What are the best 5-star hotels in Winchester?
Encore Boston Harbour, The Liberty, a Marriott Luxury Collection Hotel, Boston and XV Beacon are some of the top 5-star hotels in Winchester, according to our customer reviews. These plush hotels rate highly for things like their location, amenities and guest services. Select your favourite and enjoy the best of it all.
How much does it cost to stay in a 5-star hotel in Winchester?
How much you pay for a 5-star hotel in Winchester can vary depending on the time of year you travel and how long you plan to be away, among a range of factors. Use our price per night filter and other search tools to find the best rate on a high-end getaway.

  • Search for the lowest price per night from 6.585.745 ₫

What makes a hotel 5 stars in Winchester?
In Winchester, a hotel is required to offer a certain number of high-end amenities to earn a 5-star rating. These can include on-site gyms, gourmet restaurants, saunas and spas, premium bedding, luxury toiletries and more. What also sets 5-star hotels apart is their exceptional service. You can look forward to things like concierge services, nightly turn-down services and in-room massage. Some may also offer additional touches such as welcome gifts.