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

Find 5 Star Hotels in Winchester, MA from $209

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Our top choices for Winchester 5-star hotels

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, (4,813 reviews)
"Greta hotel, great location, Amazing staff!"
United States
Zainab
$270 nightly
The price is $315
Aug 20 - Aug 21
Total with taxes and fees
Omni Boston Hotel at the Seaport

2. Encore Boston Harbor

Encore Boston Harbor
5.0 star property
Everett
9.6 out of 10, Exceptional, (3,993 reviews)
"Great hotel - rooms very comfortable."
United States
Mark
$244 nightly
The price is $273
Aug 30 - Aug 31
Total with taxes and fees
Encore Boston Harbor

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
$404 nightly
The price is $470
Aug 30 - Aug 31
Total with taxes and fees
The Langham, Boston

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
$546 nightly
The price is $636
Aug 30 - Aug 31
Total with taxes and fees
Boston Harbor Hotel

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
$354 nightly
The price is $410
Aug 30 - Aug 31
Total with taxes and fees
The Charles Hotel

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
$285 nightly
The price is $332
Aug 30 - Aug 31
Total with taxes and fees
InterContinental Boston by IHG

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
$595 nightly
The price is $693
Aug 17 - Aug 18
Total with taxes and fees
The Newbury Boston

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
$775 nightly
The price is $903
Aug 19 - Aug 20
Total with taxes and fees
Four Seasons Hotel Boston

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
$300 nightly
The price is $349
Aug 30 - Aug 31
Total with taxes and fees
The Liberty, a Marriott Luxury Collection Hotel, Boston

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
$610 nightly
The price is $710
Aug 19 - Aug 20
Total with taxes and fees
Four Seasons Hotel One Dalton Street, Boston

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
$507 nightly
The price is $591
Aug 27 - Aug 28
Total with taxes and fees
Mandarin Oriental, Boston

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
$596 nightly
The price is $694
Aug 18 - Aug 19
Total with taxes and fees
Raffles Boston

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
$629 nightly
The price is $732
Aug 2 - Aug 3
Total with taxes and fees
The Ritz-Carlton, Boston

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
$487 nightly
The price is $567
Aug 31 - Sep 1
Total with taxes and fees
XV Beacon

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
$187 nightly
The price is $209
Aug 17 - Aug 18
Total with taxes and fees
The Bell Inn

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

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
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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.

A historic building with a clock tower, red brick walls, and a green roof.

Top Winchester Hotel Reviews

Find out more about Winchester

Ready for an incredible adventure? Add even more enjoyment on your next trip to Winchester by treating yourself to the best of the best when it comes to lodging. It's an ideal pairing. After all, you love the finer things in life, both at home and when you book a getaway. You'll join the multitudes of vacationers who have made Winchester so popular in the last year. There's no reason to delay a getaway to Winchester any longer. You can also expect excellent customer service from these hotels, so get ready to kick back and indulge. Our 5-star hotels in Winchester are the perfect places to relax in during your next getaway. You deserve the great vacation you're dreaming about.

Book the Best Winchester 5-Star Hotels

You'll have a wonderful time at one of these 5-star hotels. Excellent service, delicious meals, and personalized service are all ready for you. You're sure to find exactly the accommodation you need. You can also look forward to an outstanding experience and fantastic customer care, so get ready for a wonderful adventure. How do you want to relax? A mud wrap treatment that will leave you feeling outstanding? 24-hour room service, so you can order that Turkish coffee in the wee hours of the morning? A deep-tissue massage to help your cares fall away? Don't want to take our word for it? Explore our listings and pick the perfect accommodation for your needs.

But you aren't going to spend your entire vacation in your room, of course. We hear you. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. No matter what's on your agenda, the 5-star hotels in Winchester are waiting for you to rest up after an exciting day.

Your Getaway Starts Today

The results are in, and Winchester 5-star hotels are the place to be when you book your next vacation. If you've been dreaming about a vacation set here, then go ahead and book it. It's time to plan your next great escape -- Expedia can help you land a great deal on accommodation. Select one of our Winchester 5-star hotels today and decompress in complete comfort tomorrow.

Frequently asked questions

What are the best 5-star hotels in Winchester?
According to Expedia guest reviews, Encore Boston Harbor, The Liberty, a Marriott Luxury Collection Hotel, Boston and XV Beacon are among the most popular 5-star hotels in Winchester. Offering best-in-class amenities and unparalleled service, you can expect an opulent and memorable stay.
How much does it cost to stay in a 5-star hotel in Winchester?
You can find various pricing options for 5-star hotels in Winchester on Expedia. The amount you pay will depend on your travel dates, length of stay and other factors. Compare all of the available accommodations for your preferred dates and make use of our pricing and other filters to score the perfect high-end stay.

  • Search for the lowest price per night from $218

What makes a hotel 5 stars in Winchester?
Exemplary guest service is at the heart of every 5-star hotel in Winchester. From the moment you arrive, staff cater to your every need, whether recommending activities and tours or providing a nightly turn-down service. Additionally, hotels have to feature top-rate amenities to qualify for a 5-star rating. These can include luxury baths, saunas or spas, pools, gastronomic restaurants and knowledgeable concierge.

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