Are there any 5-star all-inclusive resorts in Winchester?

Expedia's filters are the quickest way to narrow down what you're looking for. Select "All inclusive" and "5-star" to show the finest resorts in Winchester where your room, meals, activities and entertainment are included in the upfront price. At these escapes, your trip is pure relaxation and indulgence from the moment you put down your suitcase.

What are the top 5-star spa hotels in Winchester?

Winchester has an array of 5-star spa accommodation that offer therapies designed to revitalise both the mind and body. Spend your break at Four Seasons Hotel Boston , Mandarin Oriental, Boston or Encore Boston Harbour and focus on your well-being and self-care.

Are there any 5-star holiday rentals in Winchester?

Although you won't find any 5-star holiday rentals in Winchester on our site, we have a range of stays that promise an unforgettable getaway. Discover one that matches your needs by searching our holiday rentals in Winchester .

5 Stars Hotels in Winchester

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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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.

1. Omni Boston Hotel at the Seaport

Seaport District

Rich

฿7,516 total

includes taxes & fees

22 Nov - 23 Nov

A modern bedroom with a large bed, a nightstand, a lamp, a potted plant, and a view of a cityscape at night.

2. Encore Boston Harbor

Everett

Katherine

฿9,202 total

includes taxes & fees

23 Nov - 24 Nov

The Charles Hotel with outdoor seating and a garden area.

3. The Charles Hotel

West Cambridge

Andre

฿12,923 total

includes taxes & fees

28 Nov - 29 Nov

A spacious, elegantly designed dining area with high ceilings, chandeliers, and classic decor.

4. The Langham, Boston

Downtown Boston

Mark

฿15,873 total

includes taxes & fees

28 Nov - 29 Nov

A spacious hotel lobby with a dining area, seating, large windows, and a chandelier.

5. Boston Harbor Hotel

North End

Joseph

฿19,658 total

includes taxes & fees

23 Nov - 24 Nov

A rooftop dining area with a round table set for two, surrounded by plush seating and potted plants.

6. The Newbury Boston

Back Bay

Farah

฿19,229 total

includes taxes & fees

26 Nov - 27 Nov

A modern building with a glass facade, a waterfront view, and a dock area with boats.

7. InterContinental Boston by IHG

Downtown Boston

Jo Ellen

฿8,762 total

includes taxes & fees

22 Nov - 23 Nov

A modern indoor pool area with a large window, a woman in a swimsuit, and two lounge chairs.

8. Four Seasons Hotel One Dalton Street, Boston

Fenway–Kenmore

Herbert

฿24,346 total

includes taxes & fees

23 Nov - 24 Nov

A courtyard with brick walls, outdoor seating, and potted plants.

9. Four Seasons Hotel Boston

Bay Village

Roxane

฿29,254 total

includes taxes & fees

22 Nov - 23 Nov

10. Raffles Boston

Back Bay

Mayco A Garcia

฿21,217 total

includes taxes & fees

24 Nov - 25 Nov

A modern bar area with multiple seating options, a well-stocked bar counter, and a distinctive ceiling design.

11. Mandarin Oriental, Boston

Back Bay

Matthew

฿21,845 total

includes taxes & fees

22 Nov - 23 Nov

A multi-level atrium with a central bar, seating areas, and a staircase.

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

West End

Jane

฿10,347 total

includes taxes & fees

22 Nov - 23 Nov

A spacious lobby with a central seating area, a large chandelier, and a fireplace.

13. The Ritz-Carlton, Boston

Downtown Boston

Michael

฿25,877 total

includes taxes & fees

19 Nov - 20 Nov

A hotel with a classic facade, large windows, and a prominent entrance.

14. XV Beacon

Beacon Hill

Renee

฿21,040 total

includes taxes & fees

15 Nov - 16 Nov

A spacious room with a high ceiling, large windows, and a cozy seating area with a sofa and chairs.

15. The Bell Inn

Peabody

Michelle

฿5,328 total

includes taxes & fees

23 Nov - 24 Nov

A modern interior with a pool table, green seating, and large windows offering a view of the outside.

16. Luxury Apartments by Hyatus at Boston Everett

Everett

Robert

A modern kitchen with a large island, pendant lighting, and a view of the outdoors.

17. Luxury Apartments by Hyatus Boston Somerville

Inner Belt

Yona

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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

1 Seaport Lane Boston MA

฿4,965

฿6,932 total

22 Nov - 23 Nov

includes taxes & fees

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Pool Spa Hot tub Breakfast included Waterpark

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

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 ฿6,196

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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Check availability on Winchester 5 Star Hotels

Our top choices for Winchester 5-star hotels

1. Omni Boston Hotel at the Seaport

2. Encore Boston Harbor

3. The Charles Hotel

4. The Langham, Boston

5. Boston Harbor Hotel

6. The Newbury Boston

7. InterContinental Boston by IHG

8. Four Seasons Hotel One Dalton Street, Boston

9. Four Seasons Hotel Boston

10. Raffles Boston

11. Mandarin Oriental, Boston

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

13. The Ritz-Carlton, Boston

14. XV Beacon

15. The Bell Inn

16. Luxury Apartments by Hyatus at Boston Everett

17. Luxury Apartments by Hyatus Boston Somerville

Explore similar 4-star hotels

Seaport Hotel Boston

The Westin Copley Place, Boston, a Marriott Hotel

The Dagny Boston

Learn more about Winchester

Top Winchester Hotel Reviews

Frequently asked questions

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