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.

An indoor swimming pool with a tiled ceiling, lounge chairs, and a view of the outdoors.

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

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

1. Best Western Plus New Englander

Woburn

Madison

2.943.801 ₫

3.288.225 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

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

A modern kitchen with a central island, bar seating, and a variety of food items displayed.

A modern building with large windows, outdoor seating, and a well-maintained garden.

2. Hampton Inn Boston Woburn

Woburn

Teresa D

3.397.588 ₫

3.795.106 ₫ total

includes taxes & fees

14 Nov - 15 Nov

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

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.

3. Archer Hotel Boston/Burlington

Burlington

Angelina

4.266.810 ₫

4.766.027 ₫ total

includes taxes & fees

14 Nov - 15 Nov

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

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

A restaurant with high ceilings, chandeliers, and a bar area with shelves of bottles.

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

4. Porter Square Hotel

North Cambridge

Gerardo

4.936.609 ₫

5.723.998 ₫ total

includes taxes & fees

9 Nov - 10 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 hotel with a large glass facade, a visible entrance, and a mailbox on the sidewalk.

A modern gym with a curved brown leather bench, small round tables, and woven poufs.

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

5. Hotel 1868

Agassiz

Brenda Elizabeth

4.460.318 ₫

5.171.739 ₫ total

includes taxes & fees

8 Nov - 9 Nov

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

A modern waiting area with cushioned seating, a small table with a device, and a patterned wall.

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.

6. Hampton Inn Boston Logan Airport Chelsea

Chelsea

Nicole

3.392.923 ₫

3.789.894 ₫ total

includes taxes & fees

9 Nov - 10 Nov

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

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

A breakfast buffet with various food items and a chalkboard menu.

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

7. Hampton Inn Boston Bedford Burlington

Billerica

François

2.511.260 ₫

2.805.076 ₫ 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 hotel room with a bed, a sofa, a small table, a TV, and a window with curtains.

A covered outdoor seating area with a grill, chairs, and tables.

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.

8. Sonesta Simply Suites Boston Burlington

Burlington

Cara A

2.462.020 ₫

2.750.076 ₫ total

includes taxes & fees

11 Nov - 12 Nov

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

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

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

9. Cambria Hotel Boston Somerville

Spring Hill

Mary

5.369.795 ₫

5.998.060 ₫ total

includes taxes & fees

8 Nov - 9 Nov

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

A modern lobby with a fireplace, seating area, and decorative lighting.

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

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

10. Hilton Garden Inn Boston Logan Airport

East Boston

Lisa

4.383.691 ₫

5.104.808 ₫ total

includes taxes & fees

8 Nov - 9 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.

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

A modern lounge with a large window, comfortable seating, a flat-screen TV, and a map mural on the wall.

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

11. Four Points by Sheraton Boston Newton

Newton Corner

Samantha

2.733.233 ₫

3.053.021 ₫ total

includes taxes & fees

8 Nov - 9 Nov

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

A couple walking on a sidewalk with a restaurant named "THE DAGNY" in the background.

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.

12. The Dagny Boston

Downtown Boston

Scott

5.972.735 ₫

7.860.496 ₫ total

includes taxes & fees

8 Nov - 9 Nov

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

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

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

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

13. Comfort Inn & Suites Logan International Airport

Revere

James

3.851.939 ₫

4.458.207 ₫ total

includes taxes & fees

9 Nov - 10 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 rooftop pool area with a pergola, seating, and a view of the surrounding buildings.

14. HYATT house Boston/Waltham

Waltham

Kayla

3.705.988 ₫

4.139.589 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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

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

15. Embassy Suites by Hilton Boston Waltham

Waltham

Wesly

2.656.390 ₫

2.967.188 ₫ total

includes taxes & fees

8 Nov - 9 Nov

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

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.

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

16. Hampton Inn & Suites Watertown Boston

Watertown

Emma

4.164.442 ₫

4.651.682 ₫ total

includes taxes & fees

8 Nov - 9 Nov

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

A hotel dining area with round tables and cushioned chairs, a flat-screen TV mounted on the wall, and a large window with sheer curtains.

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

4.080.215 ₫

4.557.600 ₫ total

includes taxes & fees

11 Nov - 12 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 hotel room with a large bed, a headboard with a map, and a window with curtains.

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

18. enVision Hotel Boston Everett

Everett

Angela

2.767.049 ₫

3.090.794 ₫ total

includes taxes & fees

9 Nov - 10 Nov

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

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

A modern lounge with large windows, a bar area, and seating arrangements.

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

19. Hyatt Place Boston/Seaport District

Seaport District

Levi

5.053.620 ₫

5.884.939 ₫ total

includes taxes & fees

12 Nov - 13 Nov

The exterior of the Harborside Inn Boutique Hotel with a glass entrance, numbered room 185, and two large potted plants at the entrance.

A bar area with multiple seating options including bar stools and tables, a well-stocked liquor display, and a television screen.

A spacious lounge area with a wooden floor, multiple seating options including sofas and ottomans, a television screen, and a ceiling with circular light fixtures.

A modern lobby with leather seating, tables, and a large chandelier.

20. Harborside Inn Of Boston

Downtown Boston

Sabrina

5.807.776 ₫

6.763.154 ₫ total

includes taxes & fees

8 Nov - 9 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

Encore Boston Harbor

8/10 Good

"I would have given 5+ stars. Best room I've ever had and I travel a lot. Property is beautiful, food was good, staff pleasant, etc. The reason for the 4 stars: 1 - hotel emailed about week before we were to be there and said all amenities may not be available (true, not all restaurants were open, no room service) and beware of picketing in front of property (employees were on strike); 2 - i stayed on the Harbor side 23 floor and we could still hear them beating drums late at night; 3 - it took 3 calls, 2 days and a visit to front desk to have someone to fix the TV (couldn't see the Cowboys lose) Other than that it would have been the Perfect anniversary. You would think the property would have given a voucher, discount or something. I would stay again and pay 5 star price but they need to fix the issues they have going on."

The Westin Boston Seaport District

10/10 Excellent

"Amazing would stay again"

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."

citizenM Boston Back Bay

10/10 Excellent

"Awesome hotel, great views, easy check-in and check-out, very modern. The terrace was pretty nice. Rooms are small but meet your needs, and the best part is that you can control the whole room with a tablet (AC, lights, curtains). The area where it is located also plays a good part in Newbury Street. Definitely, I would stay again."

Wyndham Boston Beacon Hill

8/10 Good

"So the doorman was fantastic !!!! Big man horrible with names but he was so helpful . When u checked in everyone was so nice …"

citizenM Boston North Station

10/10 Excellent

"Beautiful views"

Omni Parker House

10/10 Excellent

"Everything was great. The room was nice and spacious. The bathroom was great. The staff were super helpful and responsive. The food was great."

Hilton Boston Park Plaza

8/10 Good

"Beautiful hotel and very friendly staff, the room could use some updating."

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

2.675.309 ₫

3.039.947 ₫ total

26 Oct - 27 Oct

includes taxes & fees

7/10 Good! (1,287 reviews)

Lakeside Inn

595 North Ave Wakefield MA

2.815.255 ₫

3.144.640 ₫ total

8 Nov - 9 Nov

includes taxes & fees

8.2/10 Very good! (1,000 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

8/10 Very good! (522 reviews)

Best Western Plus North Shore Hotel

50 Dayton St Danvers MA

3.284.076 ₫

3.668.314 ₫ total

11 Nov - 12 Nov

includes taxes & fees

Best Western Adams Inn Quincy-Boston

29 Hancock St Quincy MA

3.475.595 ₫

3.882.240 ₫ total

12 Nov - 13 Nov

includes taxes & fees

7.8/10 Good! (1,251 reviews)

Motel 6 Danvers, MA - Boston North

65 Newbury Street/US Route 1 North Danvers MA

4.016.721 ₫

4.486.678 ₫ total

26 Oct - 27 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.

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Book Hotels in Winchester on Expedia.com

Find hotels in Winchester, MA from 2.750.076 ₫

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. Porter Square Hotel

5. Hotel 1868

6. Hampton Inn Boston Logan Airport Chelsea

7. Hampton Inn Boston Bedford Burlington

8. Sonesta Simply Suites Boston Burlington

9. Cambria Hotel Boston Somerville

10. Hilton Garden Inn Boston Logan Airport

11. Four Points by Sheraton Boston Newton

12. The Dagny Boston

13. Comfort Inn & Suites Logan International Airport

14. HYATT house Boston/Waltham

15. Embassy Suites by Hilton Boston Waltham

16. Hampton Inn & Suites Watertown Boston

17. Hampton Inn Boston - Logan Airport

18. enVision Hotel Boston Everett

19. Hyatt Place Boston/Seaport District

20. Harborside Inn Of Boston

Stay near popular Winchester attractions

Winter Pond

Griffin Photography Museum

Learn more about Winchester

Top Winchester Hotel Reviews

Encore Boston Harbor

The Westin Boston Seaport District

The Midtown Hotel MOD Collection by Sonesta

citizenM Boston Back Bay

Wyndham Boston Beacon Hill

citizenM Boston North Station

Omni Parker House

Hilton Boston Park Plaza

Hyatt Regency Boston

More cheap stays in Winchester

Motel 6 Framingham, MA - Boston West

Lakeside Inn

The Inn on Arsenal

Best Western Plus North Shore Hotel

Best Western Adams Inn Quincy-Boston

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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