Winthrop Holiday Rentals, Boston: Private House Rentals

A coastal town with a lighthouse, sandy beach, and residential buildings.

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Our top choices for Winthrop hotels

A beach view with a wooden structure and a concrete walkway.

A view from a window with a lamp in the foreground, a clear sky, and buildings across the water.

A bedroom with a large bed, a dresser, a nightstand, and a window with a view of the sea.

A balcony with a view of a house and a clear sky.

1. The Winthrop Arms Hotel And Restaurant

Winthrop

Scott

฿6,340

฿7,081 total

includes taxes & fees

2 Nov - 3 Nov

A hotel room with a bed, a desk with a lamp, a TV, and a map on the wall.

A sofa with patterned cushions and a decorative throw.

A room with a window, a radiator, a lamp, a framed picture, and a mirror.

A two-story house with a gabled roof, white siding, and a front porch with a bench.

2. Château sur Mer Bed & Breakfast

Winthrop

Jodi

฿6,344

฿7,086 total

includes taxes & fees

13 Nov - 14 Nov

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

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

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

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

3. Hilton Garden Inn Boston Logan Airport

East Boston

Lisa

฿5,678

฿6,612 total

includes taxes & fees

8 Nov - 9 Nov

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

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

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.

4. Hampton Inn Boston - Logan Airport

Revere

Rhonda

฿5,285

฿5,903 total

includes taxes & fees

11 Nov - 12 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.

5. Comfort Inn & Suites Logan International Airport

Revere

James

฿4,987

฿5,772 total

includes taxes & fees

9 Nov - 10 Nov

A waterfront patio with outdoor seating, a fire pit, and a city skyline in the background.

A modern bar area with a long counter, blue chairs, and a variety of bottles and glasses.

A restaurant with tables and chairs, a view of a city skyline across a body of water, and a brick patio area.

A gym with a treadmill, dumbbells, and a small table with apples and towels.

6. Hyatt Regency Boston Harbor

East Boston

Run

฿7,116

฿9,126 total

includes taxes & fees

1 Nov - 2 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.

7. Hyatt Place Boston/Seaport District

Seaport District

Levi

฿6,546

฿7,622 total

includes taxes & fees

12 Nov - 13 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 gym with treadmills, elliptical machines, and free weights.

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

8. Hampton Inn Boston Logan Airport Chelsea

Chelsea

Nicole

฿4,398

฿4,913 total

includes taxes & fees

10 Nov - 11 Nov

A lobby with curved seating, a central circular design on the floor, and a reception desk with a marble counter.

A person sitting by a window with a view of a cityscape.

A person sitting by a window with a city view, holding a glass.

A modern hotel lobby with a view of the city and sea, featuring comfortable seating, a small bar, and a kitchen area.

9. Renaissance® Boston Seaport District

Seaport District

Anthony

฿6,143

฿8,521 total

includes taxes & fees

30 Oct - 31 Oct

A modern hotel with a prominent Hampton Inn sign, featuring a multi-story structure with a central courtyard and a landscaped area.

A modern outdoor seating area with round tables, cushioned seating, and potted plants.

A hotel room with a bed, a desk with a TV, a chair, a sofa with a patterned pillow, and a view of a body of water and buildings.

A modern hotel lobby with a sofa, chairs, a coffee table, and a bookshelf.

10. Hampton by Hilton at the Boston Seaport District

Seaport District

Tyler

฿5,117

฿5,959 total

includes taxes & fees

1 Nov - 2 Nov

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

A woman seated in a chair reading a book in a room with a fireplace, wooden floor, and decorative wall panels.

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.

11. Seaport Hotel Boston

Seaport District

Kathleen

฿6,346

฿8,535 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 grand lobby with a large arched entrance, a high ceiling with a detailed mural, and a view of the street outside.

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

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

฿7,751

฿10,201 total

includes taxes & fees

8 Nov - 9 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 modern lobby with leather seating, tables, and a large chandelier.

An outdoor cafe with tables and chairs, a building entrance, and a street sign.

13. Harborside Inn Of Boston

Downtown Boston

Sabrina

฿7,522

฿8,760 total

includes taxes & fees

11 Nov - 12 Nov

A modern hotel with a prominent 'Avid' sign, large windows, and a well-lit entrance.

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

A city skyline with modern buildings, a river with sailboats, and a park with trees.

A modern interior with a market area, seating, and a counter.

14. avid hotel Boston Logan Airport - Revere by IHG

Revere

Louise

฿4,397

฿4,912 total

includes taxes & fees

11 Nov - 12 Nov

A spacious lobby with a large mural of a city skyline and a waterfront view.

A hotel with a modern facade, multiple floors, and a prominent entrance.

A modern indoor space with seating areas, a central staircase, and a wooden ceiling.

A modern building with a restaurant named "O'Connors" on the ground floor.

15. The Westin Boston Seaport District

Seaport District

Thomas

฿5,689

฿8,191 total

includes taxes & fees

1 Nov - 2 Nov

A modern living room with a sectional sofa, a round coffee table, and a chandelier.

Two people dining at a restaurant with various dishes and drinks on the table.

A modern living room with a gray sectional sofa, a glass coffee table, and a yellow armchair.

A hotel room with a large bed, two armchairs, a sofa, a small round table, and a mirror.

16. Hyatt Regency Boston

Downtown Boston

Allison

฿6,012

฿8,176 total

includes taxes & fees

8 Nov - 9 Nov

A modern restaurant with round tables and chairs, large windows with a city view, and a geometric patterned floor.

A modern rooftop lounge with seating and tables, a cityscape view, and a decorative wall mural.

A modern living room with a city view, featuring a sofa, armchairs, a coffee table, and a dining area.

A modern hotel lobby with a bar area, seating arrangements, and a fireplace.

17. Omni Boston Hotel at the Seaport

Seaport District

joanne

฿8,835

฿11,656 total

includes taxes & fees

11 Nov - 12 Nov

A waterfront cityscape with a variety of buildings, including a prominent clock tower and modern skyscrapers.

A waterfront hotel with outdoor seating, a view of the harbor, and a modern building with balconies.

A modern hotel room with a large bed, a seating area with a chair, a small table with a vase, and large windows offering a view of the city and water.

A modern cafe with a glass dining table, white chairs, and a coffee bar.

18. Battery Wharf Hotel, Boston Waterfront

North End

ALISON

฿8,142

฿10,853 total

includes taxes & fees

8 Nov - 9 Nov

A hotel room with a large bed, a sofa, a desk, and a view of a cityscape with a bridge.

A cityscape at dusk with illuminated buildings and a river in the background.

A modern hotel room with a grey sofa, a round wooden table, and a city view through large windows.

A modern living room with a sofa, coffee table, and bookshelves.

19. Courtyard by Marriott Boston Downtown/North Station

West End

Steve

฿8,548

฿11,131 total

includes taxes & fees

25 Oct - 26 Oct

A courtyard with string lights, outdoor seating, and a brick building facade.

A brick building with a modern entrance, a white car parked in front, and a sign indicating the entrance.

A modern bar area with wooden chairs and tables, a bar counter with bottles, and a large clock on the wall.

A modern restaurant with wooden tables and chairs, a bar area, and a mix of traditional and contemporary decor.

20. Residence Inn by Marriott Boston Downtown/Seaport

Seaport District

Richard

฿10,238

฿11,922 total

includes taxes & fees

13 Nov - 14 Nov

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Stay near popular Winthrop attractions

A lighthouse with a red, white, and blue top, a beach, and a town with houses.

Winthrop Beach

8.4/10 (26 reviews)

This tranquil stretch of shoreline offers panoramic views of Boston's skyline across the Atlantic. Stroll the promenade at sunrise when the soft sand and gentle waves create a perfect coastal escape.

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Winthrop Shore Reservation

7.6/10 (5 reviews)

This Atlantic coastal retreat offers a mix of sandy and pebbly shores with stunning Boston skyline views. Enjoy morning walks along the promenade when the beach is serene and the sea breeze most refreshing.

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Point Shirley Beach

8.0/10 (7 reviews)

Why not spend a lazy afternoon at Point Shirley Beach during your trip to Winthrop? Wander the beaches and seaside in this family-friendly area.

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Donovan Beach

7.6/10 (4 reviews)

This intimate sandy spot offers stunning Boston skyline views and a unique vantage point for watching planes from Logan Airport. Bring a picnic to enjoy while aircraft soar dramatically overhead.

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Learn more about Winthrop

This coastal gem offers spectacular Boston skyline views from Deer Island and Belle Isle Marsh Reservation. Enjoy fresh seafood at waterfront restaurants or relax on Winthrop Beach when summer temperatures rise.

See all hotels in Winthrop

A coastal town with a prominent lighthouse on a hill, surrounded by houses and greenery.

Top Winthrop 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 Winthrop

enVision Hotel Boston Everett

1834 Revere Beach Pkwy Everett MA

฿3,582

฿4,001 total

9 Nov - 10 Nov

includes taxes & fees

8.6/10 Excellent! (1,000 reviews)

Lakeside Inn

595 North Ave Wakefield MA

฿3,646

฿4,073 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

฿4,002

฿4,471 total

12 Nov - 13 Nov

includes taxes & fees

8/10 Very good! (522 reviews)

Best Western Adams Inn Quincy-Boston

29 Hancock St Quincy MA

฿4,200

฿4,691 total

8 Nov - 9 Nov

includes taxes & fees

7.8/10 Good! (1,251 reviews)

Best Western Plus North Shore Hotel

50 Dayton St Danvers MA

฿4,254

฿4,751 total

9 Nov - 10 Nov

includes taxes & fees

Motel 6 Danvers, MA - Boston North

65 Newbury Street/US Route 1 North Danvers MA

฿5,203

฿5,811 total

28 Oct - 29 Oct

includes taxes & fees

5.6/10 (1,023 reviews)

Frequently asked questions

What's the best place to stay in Winthrop?

Located 3.8 mi (6.1 km) from the heart of Winthrop, 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 Winthrop.

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

Yes, the majority of hotel room reservations are refundable if you cancel before the hotel's cancellation deadline, which often is within 24-48 hours of your arrival date. If you have a non-refundable reservation, you might still have the option to cancel and receive a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Winthrop.

What's the best place to stay for a beach holiday in Winthrop?

The Winthrop Arms Hotel And Restaurant is a top beachfront hotel with 2 bars/lounges and free WiFi, and it's located close to Revere Beach . See more stays near the beach in Winthrop.

What are some accommodation options with pools in Winthrop?

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. Another option that offers an on-site pool is Seaport Hotel Boston. View all hotels with pools in Winthrop.

What is staying in Winthrop like?

Visitors to Winthrop will definitely enjoy the beaches and restaurants. Tourists can also enjoy so much more including its cafés. Top sights around the area include Fenway Park, Faneuil Hall Marketplace and TD Garden. In Winthrop, there are 18 hotels and other accommodation options to choose from. Find out more about Winthrop.

What should I see while I'm in Winthrop?

Natural beauty is on display at Winthrop Beach, Donovan Beach and Short Beach. Additionally, you'll find Fenway Park and Faneuil Hall Marketplace in the area. Take a look at what more there is to see and do in Expedia's Winthrop guide.

What's the seasonal weather like in Winthrop?

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 1°C. Average annual precipitation for Winthrop is 1276 mm.

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Book Hotels in Winthrop on Expedia.com

Find hotels in Winthrop, MA from ฿4,001

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Winthrop

Check prices for these dates

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Our top choices for Winthrop hotels

1. The Winthrop Arms Hotel And Restaurant

2. Château sur Mer Bed & Breakfast

3. Hilton Garden Inn Boston Logan Airport

4. Hampton Inn Boston - Logan Airport

5. Comfort Inn & Suites Logan International Airport

6. Hyatt Regency Boston Harbor

7. Hyatt Place Boston/Seaport District

8. Hampton Inn Boston Logan Airport Chelsea

9. Renaissance® Boston Seaport District

10. Hampton by Hilton at the Boston Seaport District

11. Seaport Hotel Boston

12. The Dagny Boston

13. Harborside Inn Of Boston

14. avid hotel Boston Logan Airport - Revere by IHG

15. The Westin Boston Seaport District

16. Hyatt Regency Boston

17. Omni Boston Hotel at the Seaport

18. Battery Wharf Hotel, Boston Waterfront

19. Courtyard by Marriott Boston Downtown/North Station

20. Residence Inn by Marriott Boston Downtown/Seaport

Stay near popular Winthrop attractions

Winthrop Beach

Winthrop Shore Reservation

Point Shirley Beach

Donovan Beach

Learn more about Winthrop

Top Winthrop 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 Winthrop

enVision Hotel Boston Everett

Lakeside Inn

The Inn on Arsenal

Best Western Adams Inn Quincy-Boston

Best Western Plus North Shore Hotel

Motel 6 Danvers, MA - Boston North

Frequently asked questions

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