Winchester Holiday Rentals, Boston: Private House Rentals

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 hotels

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

A hotel room with a desk, two beds, a TV, a lamp, and a painting on the wall.

A modern hotel lobby with a seating area featuring blue upholstered sofas, a coffee table with a vase of flowers, and a large flat-screen TV mounted on a dark wall.

A modern hotel entrance with a covered walkway, a glass facade, and a landscaped area with shrubs and trees.

1. Best Western Plus New Englander

Woburn

Madison

2.711.515 ₫

3.028.762 ₫ total

includes taxes & fees

15 Nov - 16 Nov

A modern hotel with a covered entrance, multiple floors, and a landscaped area in front.

An indoor swimming pool with clear glass walls, wooden flooring, and blue chairs along the side.

A conference room with a long table, chairs, and pendant lighting.

A modern hotel room with a sectional sofa, armchairs, a flat-screen TV, and large windows with curtains.

2. Hampton Inn Boston Woburn

Woburn

Teresa D

3.315.175 ₫

3.703.050 ₫ total

includes taxes & fees

8 Nov - 9 Nov

A hotel lobby with a patterned carpet, a chandelier, and a seating area with blue upholstered chairs.

A pool table in a modern bar area with a brick wall and wooden ceiling.

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

3. Archer Hotel Boston/Burlington

Burlington

Angelina

4.263.024 ₫

4.761.799 ₫ total

includes taxes & fees

14 Nov - 15 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.

A modern lounge area with a brick wall, wooden paneling, and a mix of seating options including a sofa, armchairs, and ottomans.

A hotel with a large glass facade, a visible entrance, and a mailbox on the sidewalk.

A modern lounge area with wooden panel walls, two grey upholstered chairs, a round wooden table with decorative items, and a floor lamp.

4. Hotel 1868

Agassiz

Brenda Elizabeth

4.457.565 ₫

5.168.547 ₫ total

includes taxes & fees

8 Nov - 9 Nov

A bar area with wicker chairs, a bar counter, and shelves stocked with liquor bottles.

A hotel with a corner location, large windows, and a visible storefront.

A hotel room with two beds, a small table, a TV, and large windows with curtains.

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

5. Porter Square Hotel

North Cambridge

Gerardo

4.936.609 ₫

5.723.998 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

A vending machine stocked with snacks and drinks, surrounded by shelves with packaged goods.

A hotel room with a bed, a TV on a wooden stand, a desk with drawers, a microwave, and a mirror on the wall.

A gym with treadmills, elliptical machines, and free weights.

6. Hampton Inn Boston Logan Airport Chelsea

Chelsea

Nicole

3.392.404 ₫

3.789.315 ₫ total

includes taxes & fees

3 Nov - 4 Nov

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

A Hampton Inn hotel with a modern design, featuring a central entrance and multiple floors.

A gym with a bench, dumbbells, and exercise balls.

A hotel room with a bed, a sofa, a desk, and a TV.

7. Hampton Inn Boston Bedford Burlington

Billerica

François

2.509.032 ₫

2.802.589 ₫ total

includes taxes & fees

13 Nov - 14 Nov

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

A modern kitchen with dark cabinets, a black refrigerator, a microwave, and a coffee maker. There is a light-colored dining table with two chairs.

A hotel room with a bed, a sofa, a small table, a TV, and a window with curtains.

A multi-story hotel with a brick facade and a sign for 'Sonesta Simply Suites'.

8. Sonesta Simply Suites Boston Burlington

Burlington

Cara A

2.459.835 ₫

2.747.636 ₫ total

includes taxes & fees

11 Nov - 12 Nov

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

An indoor swimming pool with clear water, tiled edges, and a pool lift. There are lounge chairs and a sunshade area with umbrellas.

A hotel room with a large bed, a bedside table with a lamp, a wooden headboard, and a small desk with a telephone.

A buffet setup with various food items including fruits, vegetables, and pastries.

9. Hilton Garden Inn Boston Logan Airport

East Boston

Lee

4.379.801 ₫

5.100.279 ₫ total

includes taxes & fees

11 Nov - 12 Nov

A modern lounge area with a red sofa, bookshelves, a fireplace, and a bar area.

A restaurant with large windows, interior lighting, and seating arrangements.

A vending machine stocked with beverages in a wooden interior setting.

10. Cambria Hotel Boston Somerville

Spring Hill

Mary

4.536.454 ₫

5.067.219 ₫ total

includes taxes & fees

15 Nov - 16 Nov

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

A bar area with a long counter, multiple stools, and a neon sign.

An indoor swimming pool with a tiled floor, a wooden ceiling, and a seating area with orange cushions.

A hotel room with a four-poster bed, a desk with a laptop, a sofa, and a view of the city through the window.

11. Comfort Inn & Suites Logan International Airport

Revere

James

3.850.599 ₫

4.456.615 ₫ total

includes taxes & fees

9 Nov - 10 Nov

A restaurant with a long dining area, high ceilings, and exposed beams. Tables are set with glassware and centerpieces.

A library with leather sofas, bookshelves, and a large chandelier.

A grand lobby with a large arched entrance, a high ceiling with a detailed mural, and a view of the street outside.

A building with a sign reading "THE DAGNY" and a brick facade. There are two bicycles parked in front.

12. The Dagny Boston

Downtown Boston

Scott

5.972.735 ₫

7.860.496 ₫ total

includes taxes & fees

8 Nov - 9 Nov

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

A modern hotel with a prominent 'Hyatt House' sign, featuring a symmetrical facade, large windows, and a landscaped entrance area.

A modern kitchen with a long counter, various food items, and a large window.

A modern lobby with a sofa set, coffee table, and chairs. There are framed artworks on the wall and a large chandelier.

13. HYATT house Boston/Waltham

Waltham

Kayla

3.702.699 ₫

4.135.915 ₫ total

includes taxes & fees

15 Nov - 16 Nov

A modern lobby with a leather sofa, two round wooden tables, a flat-screen TV mounted on a textured wall, and a glass partition with a view of the outdoors.

An indoor swimming pool with clear glass walls, a tiled floor, and several chairs and tables along the side.

A classical building with a central dome and columns, surrounded by trees.

A spacious hotel lobby with multiple seating areas, including round tables and chairs, and a bar area with a counter and stools.

14. Four Points by Sheraton Boston Newton

Newton Corner

Samantha

2.619.077 ₫

2.925.508 ₫ total

includes taxes & fees

15 Nov - 16 Nov

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

A hotel room with a wooden cabinet, a sofa, a coffee table, and a TV.

A conference room with a long table, chairs, a bar area, and a television screen.

15. Embassy Suites by Hilton Boston Waltham

Waltham

Wesly

2.611.568 ₫

2.917.121 ₫ total

includes taxes & fees

8 Nov - 9 Nov

A modern living room with a fireplace, seating area, and large windows.

A modern hotel lobby with round tables, comfortable seating, large windows, and a view of the city.

A hotel room with a bed, a desk with a TV, a large window with curtains, and a city view.

A multi-story hotel with a modern design, featuring a prominent 'Hampton Inn' sign, a 'Buffalo Wild Wings' restaurant, and a 'Premier Dental' clinic.

16. Hampton Inn & Suites Watertown Boston

Watertown

Emma

4.163.405 ₫

4.650.524 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A modern bar area with a long counter, bar stools, and a television screen.

A refrigerated display with beverages and snacks, and a wall with hanging bags of groceries.

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

A hotel room with a large bed, a desk with a TV, a red armchair, a small table, and a phone on the nightstand.

17. Hampton Inn Boston - Logan Airport

Revere

Rhonda

3.630.716 ₫

4.055.510 ₫ total

includes taxes & fees

15 Nov - 16 Nov

A fireplace with decorative vases, a dining table with food and drinks, and patterned ottomans.

A Seaport Hotel with a modern entrance, large windows, and a blue awning.

A hotel room with a large window offering a city view, a television, a patterned armchair, a sofa, and a small table with a vase of flowers.

An indoor swimming pool with a skylight ceiling, seating area with cushions, and a 'No Diving' sign.

18. Seaport Hotel Boston

Seaport District

Kathleen

4.895.072 ₫

6.583.521 ₫ total

includes taxes & fees

15 Nov - 16 Nov

A modern kitchen with a bar area, wooden dining table, and bar stools.

A hotel with a modern facade, a parking lot, and two parked cars.

A brick building with a sign reading "enVision Hotel" on the corner.

A spacious lounge area with seating, a fireplace, and a bookshelf.

19. enVision Hotel Boston Everett

Everett

Angela

2.762.886 ₫

3.086.143 ₫ total

includes taxes & fees

10 Nov - 11 Nov

An outdoor seating area with a fire pit, sofas, and chairs.

A modern dining area with a view of the city, featuring a mix of seating arrangements and contemporary lighting fixtures.

A red building with a sign reading "Boston Tea Party - Ships & Museum" docked by a waterway with a tall ship and a smaller boat.

A modern building with a flat roof and large windows, situated by a calm body of water with a chain barrier in the foreground.

20. Hyatt Place Boston/Seaport District

Seaport District

Levi

5.049.135 ₫

5.879.718 ₫ total

includes taxes & fees

13 Nov - 14 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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Griffin Photography Museum

Enjoy an outing to Griffin Photography Museum during your stay in Winchester. While you're in the area, wander around the natural setting.

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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

The Revolution Hotel

8/10 Good

"Second time staying here - was in a double room last time with a friend and that was great - the single room very tight - the sink too small to really use without getting water all over. no chair or luggage rack. Clean and sparse. Liked that they had a small gym downstairs. Nice area & close to Boston Common."

Omni Boston Hotel at the Seaport

10/10 Excellent

"Great hotel"

Encore Boston Harbor

10/10 Excellent

"I like everything about this place Staff,"

Arcadian Hotel

10/10 Excellent

"Great place"

citizenM Boston Back Bay

10/10 Excellent

"Good clean hotel. Location is great"

The Dagny Boston

10/10 Excellent

"Breakfast at the Dagny is top notch! I had the SW burrito, and have had the Ham & Cheese sandie… both.. INCREDIBLE!"

The Godfrey Hotel Boston

10/10 Excellent

"Great location, great coffee shop, and very clean."

The Midtown Hotel MOD Collection by Sonesta

8/10 Good

"On te good side: Very clean, large and modern (well refreshed) room. The bed super ok. The zone is good as well. The one first lady was very helpful, the other people on staff, they are ok but it could be better. On the so-so side: That was not a breakfast. On the airplane, the quality is better. Clearly they give it just to be on paper as marketing attraction. Just don’t wake up early for that, it’s not worth it. Some noise during the night from the pipes, I assume is as much as you could change on that building. Overall, except the breakfast it’s a good choice."

Hyatt Regency Boston

10/10 Excellent

"We loved our stay here. It is right down the block from the show we saw and felt safe walking to and from. Lots of little shops and restaurants near by. Our bonus gifts from being an Expedia member were a nice touch too. Staff went above and beyond, the room was lovely and I would not hesitate to stay here again!"

More cheap stays in Winchester

Motel 6 Framingham, MA - Boston West

1668 Worcester Rd Framingham MA

2.485.469 ₫

2.828.055 ₫ total

15 Nov - 16 Nov

includes taxes & fees

Lakeside Inn

595 North Ave Wakefield MA

2.812.756 ₫

3.141.848 ₫ total

15 Nov - 16 Nov

includes taxes & fees

Best Western Adams Inn Quincy-Boston

29 Hancock St Quincy MA

3.006.436 ₫

3.358.189 ₫ total

15 Nov - 16 Nov

includes taxes & fees

7.8/10 Good! (1,252 reviews)

The Inn on Arsenal

100 N Beacon St Watertown MA

3.090.017 ₫

3.451.549 ₫ total

12 Nov - 13 Nov

includes taxes & fees

Best Western Plus North Shore Hotel

50 Dayton St Danvers MA

3.284.076 ₫

3.668.314 ₫ total

9 Nov - 10 Nov

includes taxes & fees

9/10 Wonderful! (1,001 reviews)

Motel 6 Danvers, MA - Boston North

65 Newbury Street/US Route 1 North Danvers MA

4.016.721 ₫

4.486.678 ₫ total

21 Oct - 22 Oct

includes taxes & fees

5.6/10 (1,023 reviews)

Hotels in Winchester with star rating

Frequently asked questions

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.

Explore a world of travel with Expedia

Book Hotels in Winchester on Expedia.com

Find hotels in Winchester, MA from 2.747.636 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Winchester

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Winchester hotels

1. Best Western Plus New Englander

2. Hampton Inn Boston Woburn

3. Archer Hotel Boston/Burlington

4. Hotel 1868

5. Porter Square Hotel

6. Hampton Inn Boston Logan Airport Chelsea

7. Hampton Inn Boston Bedford Burlington

8. Sonesta Simply Suites Boston Burlington

9. Hilton Garden Inn Boston Logan Airport

10. Cambria Hotel Boston Somerville

11. Comfort Inn & Suites Logan International Airport

12. The Dagny Boston

13. HYATT house Boston/Waltham

14. Four Points by Sheraton Boston Newton

15. Embassy Suites by Hilton Boston Waltham

16. Hampton Inn & Suites Watertown Boston

17. Hampton Inn Boston - Logan Airport

18. Seaport Hotel Boston

19. enVision Hotel Boston Everett

20. Hyatt Place Boston/Seaport District

Stay near popular Winchester attractions

Winter Pond

Griffin Photography Museum

Learn more about Winchester

Top Winchester Hotel Reviews

The Revolution Hotel

Omni Boston Hotel at the Seaport

Encore Boston Harbor

Arcadian Hotel

citizenM Boston Back Bay

The Dagny Boston

The Godfrey Hotel Boston

The Midtown Hotel MOD Collection by Sonesta

Hyatt Regency Boston

More cheap stays in Winchester

Motel 6 Framingham, MA - Boston West

Lakeside Inn

Best Western Adams Inn Quincy-Boston

The Inn on Arsenal

Best Western Plus North Shore Hotel

Motel 6 Danvers, MA - Boston North

Hotels in Winchester with star rating

Frequently asked questions

Explore a world of travel with Expedia

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