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

Tonight
15 Oct - 16 Oct
Tomorrow
16 Oct - 17 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

Our top choices for Winchester 5-star hotels

A modern restaurant with round tables and chairs, large windows with a city view, and a geometric patterned floor.
A modern living room with a city view, featuring a sofa, armchairs, a coffee table, and a dining area.
A modern rooftop lounge with seating and tables, a cityscape view, and a decorative wall mural.
A modern hotel lobby with a bar area, seating arrangements, and a fireplace.

1. Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport
Seaport District
United States
joanne
6.821.091 ₫
8.999.496 ₫ total
includes taxes & fees
11 Nov - 12 Nov
Omni Boston Hotel at the Seaport
A modern bedroom with a large bed, a nightstand, a lamp, a potted plant, and a view of a cityscape at night.
A modern hotel room with a large window offering a city view, a flat-screen TV, a sofa, a coffee table, and a decorative painting.
A grand hotel with a prominent marquee, a large staircase, and well-maintained gardens.
A hotel room with a large city view, a round dining table, and a sofa.

2. Encore Boston Harbor

Encore Boston Harbor
Everett
United States
Jermaine
7.231.915 ₫
8.078.049 ₫ total
includes taxes & fees
4 Nov - 5 Nov
Encore Boston Harbor
A spacious, elegantly designed dining area with high ceilings, chandeliers, and classic decor.
A grand hall with ornate ceiling and large windows.
A large, classical building with multiple windows and a prominent entrance.
A modern living room with a sofa, armchair, and coffee table, a television, and a bookshelf.

3. The Langham, Boston

The Langham, Boston
Downtown Boston
United States
Mark
12.661.677 ₫
14.744.522 ₫ total
includes taxes & fees
15 Nov - 16 Nov
The Langham, Boston
A courtyard with brick walls, outdoor seating, and potted plants.
A grand lobby with a checkered floor, green walls, and classic furniture.
A bar area with a long counter, multiple hanging lamps, and a variety of bottles and glasses.
A modern indoor pool area with large windows, comfortable seating, and a city view.

4. Four Seasons Hotel Boston

Four Seasons Hotel Boston
Bay Village
United States
Roxane
21.380.700 ₫
24.897.824 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Four Seasons Hotel Boston
The Charles Hotel with outdoor seating and a garden area.
A staircase with a modern design, featuring a combination of brick and wood elements, and a metal railing.
A hotel with a brick facade, large windows, and a prominent entrance with a glass door.
A spacious lobby with a central staircase, bookshelves, a red sofa, and a coffee table.

5. The Charles Hotel

The Charles Hotel
West Cambridge
Switzerland
Andre
9.550.115 ₫
11.073.357 ₫ total
includes taxes & fees
15 Nov - 16 Nov
The Charles Hotel
A spacious hotel lobby with a dining area, seating, large windows, and a chandelier.
A hotel room with a large bed, a TV, a desk, and a view of the sea.
A cityscape with modern high-rise buildings, a central roundabout, and a mix of commercial and residential structures.
A room with a large window overlooking a marina, featuring a sofa set, two side tables, and a patterned rug.

6. Boston Harbor Hotel

Boston Harbor Hotel
North End
United States
Dorothy
15.747.453 ₫
18.352.161 ₫ total
includes taxes & fees
30 Oct - 31 Oct
Boston Harbor Hotel
A rooftop dining area with a round table set for two, surrounded by plush seating and potted plants.
A park with a lamp post, a bridge, and buildings in the background.
A bar area with marble countertops, blue bar stools, and a variety of bottles.
A spacious living room with a large sofa, two armchairs, a coffee table, and a dining area with a table and chairs.

7. The Newbury Boston

The Newbury Boston
Back Bay
United States
Farah
15.303.139 ₫
19.178.504 ₫ total
includes taxes & fees
1 Nov - 2 Nov
The Newbury Boston
A modern building with a glass facade, a waterfront view, and a dock area with boats.
A spacious, well-lit event space with a reflective floor, large windows, and elegant floral centerpieces.
A table with a variety of food and drink items, including a bottle of champagne, glasses, and macarons, set against a cityscape view.
A modern lobby with a central seating area, a reception desk, and a distinctive geometric light fixture.

8. InterContinental Boston by IHG

InterContinental Boston by IHG
Downtown Boston
United States
Stepan S
7.690.221 ₫
10.131.322 ₫ total
includes taxes & fees
15 Nov - 16 Nov
InterContinental Boston by IHG
A modern indoor pool area with a large window, a woman in a swimsuit, and two lounge chairs.
A modern rooftop terrace with wicker furniture, a glass balustrade, and a view of historic buildings.
A hotel room with a large window offering a city view, a bed, a chair, and a small table with a tray.
A modern bathroom with a large bathtub, a glass shower enclosure, and a view of a cityscape through large windows.

9. Four Seasons Hotel One Dalton Street, Boston

Four Seasons Hotel One Dalton Street, Boston
Fenway–Kenmore
United States
Masooda
17.218.845 ₫
20.051.344 ₫ total
includes taxes & fees
10 Nov - 11 Nov
Four Seasons Hotel One Dalton Street, Boston
A modern bar area with multiple seating options, a well-stocked bar counter, and a distinctive ceiling design.
A lobby with a central round table, potted plants, and artwork on the walls.
A modern restaurant with round tables, white cushioned seating, and circular ceiling lights.
A modern lounge with two sofas, a fireplace, and a unique ceiling chandelier.

10. Mandarin Oriental, Boston

Mandarin Oriental, Boston
Back Bay
United States
Matthew
17.104.560 ₫
19.918.259 ₫ total
includes taxes & fees
8 Nov - 9 Nov
Mandarin Oriental, Boston
Pool
A modern hotel room with a large window, a sofa, a red armchair, a round coffee table, and a bed with a view of the cityscape.
A modern living room with a fireplace, comfortable seating, a large window with a city view, and a chandelier.
A modern lobby with a staircase, seating area, and large windows offering city views.

11. Raffles Boston

Raffles Boston
Back Bay
United States
Vlatko
15.432.228 ₫
17.970.830 ₫ total
includes taxes & fees
15 Nov - 16 Nov
Raffles Boston
A multi-level atrium with a central bar, seating areas, and a staircase.
A multi-level interior with hanging greenery and a bar area.
An outdoor seating area with white and yellow chairs, surrounded by trees and a stone building with arched windows.
A spacious lobby with a high ceiling, a large chandelier, and a seating area with leather chairs.

12. The Liberty, a Marriott Luxury Collection Hotel, Boston

The Liberty, a Marriott Luxury Collection Hotel, Boston
West End
United States
Gabrielle
8.039.777 ₫
10.116.065 ₫ total
includes taxes & fees
1 Nov - 2 Nov
The Liberty, a Marriott Luxury Collection Hotel, Boston
A hotel with a classic facade, large windows, and a prominent entrance.
A hotel room with a large bed, a sofa, a desk, a television, and a fireplace.
A modern living room with a fireplace, two armchairs, a coffee table, and a zebra-patterned rug.
A modern living room with a fireplace, two armchairs, a sofa, a zebra-patterned rug, and a staircase leading to an upper floor.

13. XV Beacon

XV Beacon
Beacon Hill
United States
Renee
13.865.701 ₫
16.146.607 ₫ total
includes taxes & fees
1 Nov - 2 Nov
XV Beacon
A modern hotel room with a large window offering a city view, a sofa with patterned cushions, a round table, a desk with a chair, and a lamp.
A luxurious living room with a fireplace, leather sofas, and a patterned carpet.
A person sitting by a window with a cityscape view, a breakfast tray, and a cup.
A bar area with multiple shelves of bottles and glasses, bar stools, and a warm, well-lit ambiance.

14. The Ritz-Carlton, Boston

The Ritz-Carlton, Boston
Downtown Boston
United States
Michael
18.115.284 ₫
22.302.532 ₫ total
includes taxes & fees
8 Nov - 9 Nov
The Ritz-Carlton, Boston
A spacious room with a high ceiling, large windows, and a cozy seating area with a sofa and chairs.
A building with a sign reading "THE CELLAR" and a wooden gate.
A modern kitchen with white cabinets, stainless steel appliances, and a tiled floor.
A room with a white wall-mounted lamp, a window with curtains, a sofa, and a patterned chair.

15. The Bell Inn

The Bell Inn
Peabody
United States
Paul
3.662.666 ₫
4.091.198 ₫ total
includes taxes & fees
2 Nov - 3 Nov
The Bell Inn
A modern interior with a pool table, green seating, and large windows offering a view of the outside.
A spacious lobby with large windows, a central seating area with sofas and chairs, and a modern design with a large screen on the wall.
A spacious lobby with a modern design, featuring a curved seating area, a central fire feature, and a mix of seating options including sofas and chairs.
An aerial view of a hotel courtyard with a swimming pool, outdoor seating, and greenery.

16. Luxury Apartments by Hyatus at Boston Everett

Luxury Apartments by Hyatus at Boston Everett
Everett
United States
Robert
Luxury Apartments by Hyatus at Boston Everett
A modern kitchen with a large island, pendant lighting, and a view of the outdoors.
A modern kitchen with a central island, bar stools, and a fireplace.
A spacious dining area with a large wooden table, six wooden stools, and a modern chandelier.
A modern living room with a sectional sofa, a fireplace, and large windows offering a view of the outdoors.

17. Luxury Apartments by Hyatus Boston Somerville

Luxury Apartments by Hyatus Boston Somerville
Inner Belt
United States
Yona
Luxury Apartments by Hyatus Boston Somerville
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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
4.895.072 ₫
6.583.521 ₫ total
15 Nov - 16 Nov
includes taxes & fees
Seaport Hotel Boston
Hilton Boston Park Plaza

Hilton Boston Park Plaza

50 Park Plaza Boston MA
5.040.072 ₫
6.924.304 ₫ total
8 Nov - 9 Nov
includes taxes & fees
Hilton Boston Park Plaza
The Westin Copley Place, Boston, a Marriott Hotel

The Westin Copley Place, Boston, a Marriott Hotel

10 Huntington Ave Boston MA
7.022.182 ₫
9.232.730 ₫ total
30 Oct - 31 Oct
includes taxes & fees
The Westin Copley Place, Boston, a Marriott Hotel
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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
An aerial view of a town with a lake, church steeples, and a bridge.

Top Winchester Hotel Reviews

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

10/10 Excellent
"Great view of the city."
Jodiann 1-night trip
Posted less than an hour 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 6.583.521 ₫
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.

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