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

5 Stars Hotels in Winchester

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Winchester 5 Star Hotels

This weekend
31 Jul - 2 Aug
Next weekend
7 Aug - 9 Aug

Our top choices for Winchester 5-star hotels

4 restaurants; breakfast, lunch and dinner served

1. Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport
5.0 star property
Seaport District
9.2 out of 10, Wonderful, (4,809 reviews)
"Greta hotel, great location, Amazing staff!"
United States
Zainab
The price is ฿8,274
฿10,995 total
includes taxes & fees
6 Aug - 7 Aug
Omni Boston Hotel at the Seaport
Apartment, 2 Bedrooms | Premium bedding, down duvets, pillow-top beds, minibar

2. Encore Boston Harbor

Encore Boston Harbor
5.0 star property
Everett
9.6 out of 10, Exceptional, (3,991 reviews)
"Great hotel - rooms very comfortable."
United States
Mark
The price is ฿11,649
฿13,012 total
includes taxes & fees
30 Aug - 31 Aug
Encore Boston Harbor
Breakfast, lunch and brunch served

3. The Langham, Boston

The Langham, Boston
5.0 star property
Downtown Boston
9.6 out of 10, Exceptional, (1,000 reviews)
"I LOVED EVERYTHING about this hotel. The staff was amazing. Great location and great amenities"
United States
Rhonda
The price is ฿14,186
฿16,519 total
includes taxes & fees
30 Aug - 31 Aug
The Langham, Boston
Suite, Multiple Beds (John Adams Presidential Suite) | Frette Italian sheets, premium bedding, pillow-top beds, minibar

4. Boston Harbor Hotel

Boston Harbor Hotel
5.0 star property
North End
9.8 out of 10, Exceptional, (1,002 reviews)
"Great location and very helpful staff"
United States
John
The price is ฿16,384
฿19,097 total
includes taxes & fees
30 Aug - 31 Aug
Boston Harbor Hotel
3 restaurants; breakfast, lunch, dinner and brunch served

5. The Charles Hotel

The Charles Hotel
5.0 star property
West Cambridge
9.4 out of 10, Exceptional, (1,003 reviews)
"Great location"
United States
Carmen
The price is ฿11,801
฿13,683 total
includes taxes & fees
30 Aug - 31 Aug
The Charles Hotel
Exterior

6. InterContinental Boston by IHG

InterContinental Boston by IHG
5.0 star property
Downtown Boston
9.4 out of 10, Exceptional, (1,148 reviews)
"Great hotel and good location"
Canada
Kaelyn
The price is ฿9,022
฿12,030 total
includes taxes & fees
23 Aug - 24 Aug
InterContinental Boston by IHG
Lunch and dinner served

7. The Newbury Boston

The Newbury Boston
5.0 star property
Back Bay
9.4 out of 10, Exceptional, (699 reviews)
"Great location and great staff!"
United States
Tae Hwan
The price is ฿18,358
฿23,126 total
includes taxes & fees
16 Aug - 17 Aug
The Newbury Boston
Terrace/patio

8. Four Seasons Hotel Boston

Four Seasons Hotel Boston
5.0 star property
Bay Village
9.4 out of 10, Exceptional, (475 reviews)
"The best hotel in Boston "
United States
Madina
The price is ฿25,868
฿30,123 total
includes taxes & fees
19 Aug - 20 Aug
Four Seasons Hotel Boston
Property amenity

9. 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, (1,003 reviews)
"Great place in a great location! Staff was great"
United States
Donald
The price is ฿9,179
฿11,661 total
includes taxes & fees
30 Aug - 31 Aug
The Liberty, a Marriott Luxury Collection Hotel, Boston
Indoor pool, open 6:00 AM to 9:00 PM, pool loungers

10. Four Seasons Hotel One Dalton Street, Boston

Four Seasons Hotel One Dalton Street, Boston
5.0 star property
Fenway–Kenmore
9.6 out of 10, Exceptional, (426 reviews)
"Excellent service, great location and very friendly staff"
United States
Omar
The price is ฿20,361
฿23,710 total
includes taxes & fees
19 Aug - 20 Aug
Four Seasons Hotel One Dalton Street, Boston
Breakfast, lunch and dinner served

11. Mandarin Oriental, Boston

Mandarin Oriental, Boston
5.0 star property
Back Bay
9.4 out of 10, Exceptional, (438 reviews)
"The location is fantastic. That’s the best part. The hotel is a bit tired and can use a refresh."
Canada
Alex
The price is ฿16,939
฿19,725 total
includes taxes & fees
27 Aug - 28 Aug
Mandarin Oriental, Boston
Indoor pool

12. Raffles Boston

Raffles Boston
5.0 star property
Back Bay
9.6 out of 10, Exceptional, (284 reviews)
"Amazing staff, excellent food. Wish my stay was longer."
United States
Ryan
The price is ฿19,722
฿22,966 total
includes taxes & fees
18 Aug - 19 Aug
Raffles Boston
Reception

13. The Ritz-Carlton, Boston

The Ritz-Carlton, Boston
5.0 star property
Downtown Boston
9.0 out of 10, Wonderful, (474 reviews)
"Great hotel, great food and friendly staff "
United States
Oswaldo
The price is ฿20,995
฿24,448 total
includes taxes & fees
2 Aug - 3 Aug
The Ritz-Carlton, Boston
Exterior

14. 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 ฿17,874
฿20,814 total
includes taxes & fees
9 Aug - 10 Aug
XV Beacon
Honeymoon Room | In-room dining

15. The Bell Inn

The Bell Inn
5.0 star property
Peabody
9.2 out of 10, Wonderful, (270 reviews)
"Awesome place to stay!!"
United States
Joseph A
The price is ฿7,318
฿8,175 total
includes taxes & fees
3 Aug - 4 Aug
The Bell Inn
Billiards

16. Luxury Apartments by Hyatus at Boston Everett

Luxury Apartments by Hyatus at Boston Everett
5.0 star property
Everett
9.0 out of 10, Wonderful, (6 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
Lounge

17. Luxury Apartments by Hyatus Boston Somerville

Luxury Apartments by Hyatus Boston Somerville
5.0 star property
Inner Belt
10.0 out of 10, Exceptional, (4 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
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.
Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

575 Memorial Drive Cambridge MA
The price is ฿6,286 per night from 9 Aug to 10 Aug
฿6,286
฿8,285 total
9 Aug - 10 Aug
includes taxes & fees
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.

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
"Cool room and view and good location. Room was not cleaned well though"
Danielle 3-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 ฿7,358

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.