𝗧𝗢𝗣 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Winchester from RM271 (2026) - Fully Refundable Options

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Our top choices for Winchester hotels

A modern restaurant with a central counter, multiple dining tables, and chairs.

1. Best Western Plus New Englander

Woburn

William

RM475 total

includes taxes & fees

15 Nov - 16 Nov

A spacious lobby with a reception desk, seating area, and a staircase leading to an upper level.

2. Hampton Inn Boston Bedford Burlington

Billerica

G.

RM478 total

includes taxes & fees

28 Nov - 29 Nov

A spacious lobby with a mix of seating areas, a fireplace, and large windows providing natural light.

3. Archer Hotel Boston/Burlington

Burlington

Marius

RM715 total

includes taxes & fees

22 Nov - 23 Nov

A spacious lobby with a high ceiling, wooden paneling, a large sofa, and a coffee table.

4. Comfort Inn & Suites Logan International Airport

Revere

William

RM562 total

includes taxes & fees

26 Nov - 27 Nov

An outdoor patio area with a fire pit, seating, and a grill.

5. HYATT house Boston/Waltham

Waltham

Efrain

RM485 total

includes taxes & fees

20 Nov - 21 Nov

A modern living room with a sofa, a dining table, and chairs. There is a kitchen area with cabinets and a microwave.

6. Sonesta Simply Suites Boston Burlington

Burlington

Marco

RM385 total

includes taxes & fees

24 Nov - 25 Nov

A modern living room with a fireplace, a dining area, and a bar with stools.

7. Hampton Inn Boston Logan Airport Chelsea

Chelsea

Edwin J Ruiz

RM497 total

includes taxes & fees

24 Nov - 25 Nov

A modern cafe with a central island, seating area, and a beverage display.

8. enVision Hotel Boston Everett

Everett

Lisette

RM445 total

includes taxes & fees

23 Nov - 24 Nov

A modern building with a courtyard, benches, and flower beds.

9. Porter Square Hotel

North Cambridge

Gerardo

RM527 total

includes taxes & fees

22 Nov - 23 Nov

A spacious lobby with a grey sofa set, a coffee table, and a dining area in the background.

10. avid hotel Boston Logan Airport - Revere by IHG

Revere

Carleen

RM467 total

includes taxes & fees

8 Dec - 9 Dec

A modern bar area with a long counter, multiple seating options, and large windows providing views of the outside.

11. Cambria Hotel Boston Somerville

Spring Hill

Mary

RM613 total

includes taxes & fees

22 Nov - 23 Nov

A modern living room with a fireplace, two armchairs, a coffee table, and a striped rug.

12. Hampton Inn Boston - Logan Airport

Revere

Paul

RM457 total

includes taxes & fees

5 Dec - 6 Dec

An indoor swimming pool with clear water, surrounded by windows and covered by large, neutral-colored canopies.

13. Best Western Plus Waltham Boston

Piety Corner

carrie

RM359 total

includes taxes & fees

29 Nov - 30 Nov

A hotel with a swimming pool, parking lot, and a view of a lake.

14. Lakeside Inn

Wakefield

Richard

RM391 total

includes taxes & fees

15 Nov - 16 Nov

A cozy living room with a leather sofa, a white armchair, and a coffee table. There are framed botanical illustrations on the wall and a large window with hanging glass terrariums.

15. Hotel 1868

Agassiz

Megan B

RM572 total

includes taxes & fees

29 Nov - 30 Nov

A spacious lobby with a central seating area, multiple levels, and a fountain.

16. Hilton Boston Logan Airport

East Boston

Leslie

RM735 total

includes taxes & fees

6 Dec - 7 Dec

A modern kitchen with a central island, bar stools, and a dining area with a large table.

17. Hampton Inn & Suites Boston/Waltham

Waltham

Rachel

RM443 total

includes taxes & fees

6 Dec - 7 Dec

A Hilton Garden Inn hotel with a modern design, featuring a large signboard with the hotel's name.

18. Hilton Garden Inn Boston Logan Airport

East Boston

Andrew

RM558 total

includes taxes & fees

6 Dec - 7 Dec

A spacious indoor area with a long dining table, multiple seating arrangements, and a ceiling with hanging lights.

19. Embassy Suites by Hilton Boston Waltham

Waltham

John

RM442 total

includes taxes & fees

6 Dec - 7 Dec

A modern hotel reception area with two reception desks, a large flat-screen TV mounted on the wall, and a ceiling with recessed lighting and circular light fixtures.

20. Hilton Garden Inn Boston/Waltham

Waltham

Cathy

RM420 total

includes taxes & fees

6 Dec - 7 Dec

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Hotels recommended for families in Winchester

Best Western Plus New Englander

Woburn

RM475 total

includes taxes & fees

15 Nov - 16 Nov

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Stay near popular Winchester attractions

Winter Pond

9.0/10 (2 reviews)

Winter Pond offers a tranquil escape as Massachusetts' northernmost Coastal Plain Pondshore Community. Bring binoculars to spot diverse bird species while strolling along its peaceful shores.

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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

An aerial view of a town with a lake, church steeples, and a bridge.

Top Winchester Hotel Reviews

Harborside Inn Of Boston

8/10 Good

"Great location and helpful staff. Would want a room with an outside window next time."

citizenM Boston North Station

8/10 Good

"Fun place to stay and in good location just quirky things that are not convenient… the mini fridge was just a “cooler” and very small so it was not meant to chill anything and couldn’t have left overs… staying several nights would have been nice to keep cold drinks and snacks… everything such as lights, tv, the curtains were controlled by an iPad- curtains got hung up, iPad was slow at times, one switch turned everything off. Faucet was loose as floating toilet moved when you sat on it like it was going to come off the wall. Very small and no privacy for the bathroom/shower at all."

More cheap stays in Winchester

Methuen Inn and Conference Center

159 Pelham Street Methuen MA

RM243

RM271 total

12 Nov - 13 Nov

includes taxes & fees

Frequently asked questions

What's the best place to stay in Winchester?

Located 8.7 mi (14 km) from the heart of Winchester, Omni Boston Hotel at the Seaport is a top choice for your stay, based on our traveller data. Two other options for your stay in the area are Seaport Hotel Boston and The Revolution Hotel. See all available top hotels, or vacation rentals in Winchester.

If I need to cancel my hotel reservation in Winchester, will I receive a refund?

Yes, most hotel bookings are fully refundable if cancelled before the hotel's cancellation deadline, which is often 24 or 48 hours before the scheduled arrival. If you have a non-refundable reservation, it may still be possible to cancel it and get a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.

What are some accommodation options with pools in Winchester?

Omni Boston Hotel at the Seaport: Hotel, 2-minute walk from Boston Convention and Exhibition Center. Features 4 restaurants, an outdoor pool and a full-service spa. Also, another option with an on-site pool is Seaport Hotel Boston. View all hotels with pools in Winchester.

What is staying in Winchester like?

Visitors can enjoy all that Winchester has to offer, including the football matches and lake views. Fenway Park, Encore Boston Harbor and Harvard Square are some of the top sights around the area. In Winchester, there are 6 hotels and other accommodation options to choose from. Find out more about Winchester.

What should I do while I'm visiting Winchester?

Favourite places to visit include Winter Pond, Middlesex Fells Reservation and Griffin Photography Museum. Additionally, you'll find Fenway Park and Encore Boston Harbor in the area. Take a look at what more there is to see and do in Expedia's Winchester guide.

How can I get around Winchester?

To venture out into the surrounding area, ride one of the trains from Winchester Station or Winchester Wedgemere Station. If you want to venture out around the area, you may want a rental car in Winchester for your journey.

What's the weather like in Winchester?

The hottest months are usually July and August, with an average temperature of 21°C, while the coldest months are January and February, with an average of 0°C. The snowiest months in Winchester are January, February, March and April, with each month seeing an average of 13 cm of snowfall.

Winchester hotels from RM271

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Our top choices for Winchester hotels

1. Best Western Plus New Englander

2. Hampton Inn Boston Bedford Burlington

3. Archer Hotel Boston/Burlington

4. Comfort Inn & Suites Logan International Airport

5. HYATT house Boston/Waltham

6. Sonesta Simply Suites Boston Burlington

7. Hampton Inn Boston Logan Airport Chelsea

8. enVision Hotel Boston Everett

9. Porter Square Hotel

10. avid hotel Boston Logan Airport - Revere by IHG

11. Cambria Hotel Boston Somerville

12. Hampton Inn Boston - Logan Airport

13. Best Western Plus Waltham Boston

14. Lakeside Inn

15. Hotel 1868

16. Hilton Boston Logan Airport

17. Hampton Inn & Suites Boston/Waltham

18. Hilton Garden Inn Boston Logan Airport

19. Embassy Suites by Hilton Boston Waltham

20. Hilton Garden Inn Boston/Waltham

Hotels recommended for families in Winchester

Best Western Plus New Englander

Stay near popular Winchester attractions

Winter Pond

Learn more about Winchester

Top Winchester Hotel Reviews

Harborside Inn Of Boston

More cheap stays in Winchester

Methuen Inn and Conference Center

Frequently asked questions

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