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Top Holiday Rentals in Winthrop

North East Downtown Boston Rentals

North East Downtown Boston Rentals

3 out of 5
257 Hanover St, Boston, MA
The price is £228 per night from 26 Apr to 27 Apr

Located in North End, this apartment building is steps away from Paul Revere House and The Freedom Trail. Boston Harbor and Faneuil Hall Marketplace are also ...

North East Downtown Boston Rentals
Sonder - Pierce Boston

Sonder - Pierce Boston

4 out of 5
Brookline Avenue, Boylston St, Boston, MA
The price is £162 per night from 27 Apr to 28 Apr

Located in Fenway–Kenmore, this apartment building is within a 10-minute walk of Longwood Medical Area, Fenway Park and Beth Israel Deaconess Medical Center. ...

4.4/5Excellent! (69 reviews)

"I liked the views. I didn’t like having to use chrome cast for tv. And we couldn’t get any local stations or normal tv. Only able to do Netflix and Amazon"…"

Reviewed on 18 Feb 2021

Sonder - Pierce Boston
Convenient and Cozy 2 Bedroom Near Assembly Row-3rd Floor

Convenient and Cozy 2 Bedroom Near Assembly Row-3rd Floor

20, SARGENT AVENUE, 3, Somerville, MA

Located in Winter Hill, this apartment building is within 1 mi (2 km) of Assembly Row and LEGOLAND® Discovery Center Boston. Harvard University and Harvard Square ...

4/5Very Good! (3 reviews)
Horrible

"Lol are you serious"…"

Reviewed on 22 Sep 2020

Convenient and Cozy 2 Bedroom Near Assembly Row-3rd Floor
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Sonder - Hancock Suites

Sonder - Hancock Suites

3.5 out of 5
40 Hancock Street, Boston, MA

Located in Beacon Hill, this aparthotel is within a 5-minute walk of Massachusetts State House and The Freedom Trail. Boston Common and Massachusetts General ...

4.4/5Excellent! (16 reviews)

"Great apartment even better staff! So helpful and nice !!"…"

Reviewed on 10 Feb 2020

Sonder - Hancock Suites
Theater District 30 Day Stays 2bedroom den

Theater District 30 Day Stays 2bedroom den

1 Nassau St, Boston, MA
The price is £234 per night from 14 Apr to 15 Apr

Located in Chinatown, this apartment building is within a 10-minute walk of Tufts Medical Center, Boston Opera House and Boch Center. Charles Playhouse and Wilbur ...

5/5Exceptional! (1 review)
Perfect location

"I was not familiar with Boston so I was nervous about location. It ended up being perfect. Easy to navigate to either driving or walking. Clean, beautiful and so convenient. Thank you."…"

Reviewed on 2 Apr 2021

Theater District 30 Day Stays 2bedroom den
Charlestown Houseboat Walk to Attractions Be Rocked to Sleep

Charlestown Houseboat Walk to Attractions Be Rocked to Sleep

Pier 8 13th Street, Boston, MA
The price is £419 per night from 14 Apr to 15 Apr

Located in Charlestown, this houseboat is within a 10-minute walk of The Freedom Trail and USS Constitution Museum. Boston Harbor and Bunker Hill Monument are ...

4.7/5Exceptional! (9 reviews)
White pearl

"All as advertised. Enjoyed thoroughly"…"

Reviewed on 19 Oct 2020

Charlestown Houseboat Walk to Attractions Be Rocked to Sleep
Near Scenic Fresh Pond, Charles River, Shops, Harvard Sq Access , Free Parking

Near Scenic Fresh Pond, Charles River, Shops, Harvard Sq Access , Free Parking

87 Fresh Pond Pkwy, 2nd Floor Studio Apartment, Cambridge, MA

Located in West Cambridge, this historic apartment building is within 3 miles (5 km) of Harvard University, Harvard Square and Brighton Music Hall. Tufts University ...

4.3/5Excellent! (35 reviews)
Great location, charming neighborhood

"Location was great. Apartment was not as clean as I would have expected. Bathroom had a distinct smell and sheets and pillows had stains on them."…"

Reviewed on 3 Sep 2019

Near Scenic Fresh Pond, Charles River, Shops, Harvard Sq Access , Free Parking
Stunning Beach House- Cross the Street to the Beach

Stunning Beach House- Cross the Street to the Beach

540 Revere Beach Blvd, 342, Revere, MA

Located in the heart of Revere, this apartment building is 0.1 mi (0.1 km) from Revere Beach and within 9 miles (15 km) of TD Garden and Boston Harbor. Boston ...

5/5Exceptional! (4 reviews)
We would rent again

"We enjoyed our stay and Andrew was very accommodating."…"

Reviewed on 22 Mar 2021

Stunning Beach House- Cross the Street to the Beach
Come Float in Boston Harbor on a 45 Foot Yacht! Plenty of Fresh Air!

Come Float in Boston Harbor on a 45 Foot Yacht! Plenty of Fresh Air!

Pier 8, end of 13th Street, Boston, MA
The price is £387 per night from 14 Apr to 15 Apr

Located in Charlestown, this houseboat is within a 15-minute walk of The Freedom Trail and USS Constitution Museum. Boston Harbor and Bunker Hill Monument are ...

5/5Exceptional! (7 reviews)
Anchor me inn!

"Small world. Owner used to live near us in Pittsburgh! Clean & comfortable!"…"

Reviewed on 1 Oct 2020

Come Float in Boston Harbor on a 45 Foot Yacht! Plenty of Fresh Air!
Fun Houseboat. Walk to Boston Attractions Wifi

Fun Houseboat. Walk to Boston Attractions Wifi

13 street, 1, Boston, MA
The price is £419 per night from 14 Apr to 15 Apr

Located in Charlestown, this houseboat is within a 15-minute walk of The Freedom Trail and USS Constitution Museum. Boston Harbor and Bunker Hill Monument are ...

4.8/5Exceptional! (4 reviews)
Loved it. Great location.

"Amazing location. So nice to have parking at the dock. Owners quick to respond. I mentioned the coffee pot cord didn’t reach the outlet At night and next morning there was an extension cord! So enjoyed drinks on both decks!! WiFi is really weak. Steaming not allowed but we never had the tv on! The ..."…"

Reviewed on 6 Oct 2020

Fun Houseboat. Walk to Boston Attractions Wifi
Ocean 2br apt in Seaport Boston Steps From Downtown

Ocean 2br apt in Seaport Boston Steps From Downtown

399 Congress St, 1724, Boston, MA
The price is £434 per night from 18 Apr to 19 Apr

Located in Seaport District, this holiday home is within a 10-minute walk of Institute of Contemporary Art, Boston Convention and Exhibition Center and Boston ...

Ocean 2br apt in Seaport Boston Steps From Downtown
Picturesque Cottage With Enclosed Deck - Close to Salem & the Ocean!

Picturesque Cottage With Enclosed Deck - Close to Salem & the Ocean!

2 Melvin Avenue, Beverly, MA

Situated in Beverly, this holiday home is within 3 miles (5 km) of Lacrom Theatre, John Cabot House and Massachusetts Bay. Dane Street Beach and Lynch Park are ...

4/5Very Good! (1 review)
Home Away From Home

"We stayed at the Riverview Cottage to visit family in the area. We appreciated the cottage’s quiet location next to the river and it’s convent distance from family. We were cozy in the home, especially in the king-size bed and the big couch in the living room. We also really enjoyed having relaxed ..."…"

Reviewed on 31 Aug 2020

Picturesque Cottage With Enclosed Deck - Close to Salem & the Ocean!
Quaint Beverly Townhome: Walk to Beach & Downtown!

Quaint Beverly Townhome: Walk to Beach & Downtown!

39 Central Street, Beverly, MA

Located in the heart of Beverly, this holiday home is 0.1 mi (0.2 km) from Massachusetts Bay and within 3 miles (5 km) of Salem Witch Museum and Salem Witch ...

4.8/5Exceptional! (13 reviews)
Loved it

"Excellent"…"

Reviewed on 20 Oct 2020

Quaint Beverly Townhome: Walk to Beach & Downtown!
New! Cozy Boston Area Home < 1 Mi to Revere Beach!

New! Cozy Boston Area Home < 1 Mi to Revere Beach!

27 Flint Street, Revere, MA

Situated in Revere, this holiday home is 0.5 mi (0.8 km) from Revere Beach and within 9 miles (15 km) of Encore Boston Harbor and TD Garden. Boston Harbor and ...

5/5Exceptional! (1 review)
Great place for a getaway!

"Really lovely place to stay. Clean, organized, and comfy!"…"

Reviewed on 17 Mar 2021

New! Cozy Boston Area Home < 1 Mi to Revere Beach!
Waterside Boston 30 Day Stays Two Bedroom

Waterside Boston 30 Day Stays Two Bedroom

111 Atlantic Ave, Boston, MA
The price is £261 per night from 3 May to 4 May

Located in North End, this apartment building is steps away from Long Wharf and Boston Harbor. The Freedom Trail and New England Aquarium are also within 5 minutes. ...

Waterside Boston 30 Day Stays Two Bedroom
Mermaid of Hull ~ Looking at Nantasket Beach ~ Events Allowed

Mermaid of Hull ~ Looking at Nantasket Beach ~ Events Allowed

278 Nantasket Ave, Hull, MA

Located in Hull, this beachfront holiday home is in the city centre, 0.2 mi (0.3 km) from Nantasket Beach, and within 12 mi (20 km) of Wollaston Beach and South ...

4.8/5Exceptional! (15 reviews)
Amazing Place with Stunning views and Ocean Access!

"The Mermaid of the Hull was a beautiful property! I came here with a few friends for my birthday and it was perfect. The views from the rooftop patio are amazing and the beach access is awesome. I highly recommend waking up early to see the sun rising over the bay! Everything was just as I could’ve ..."…"

Reviewed on 1 Apr 2021

Mermaid of Hull ~ Looking at Nantasket Beach ~ Events Allowed
High Luxury apt in Boston Seaport

High Luxury apt in Boston Seaport

399 Congress St, 1228, Boston, MA
The price is £529 per night from 19 Apr to 20 Apr

Located in Seaport District, this apartment building is within a 10-minute walk of Institute of Contemporary Art, Boston Convention and Exhibition Center and ...

5/5Exceptional! (1 review)
lovely weekend in boston

"clean and convenient."…"

Reviewed on 23 Mar 2021

High Luxury apt in Boston Seaport
Visit Boston on Green Turtle Houseboat in Boston Harbor! Plenty of Fresh Air

Visit Boston on Green Turtle Houseboat in Boston Harbor! Plenty of Fresh Air

1 Pier 8, Boston, MA
The price is £266 per night from 14 Apr to 15 Apr

This family-friendly Boston houseboat is located on the waterfront, within a 15-minute walk of USS Constitution Museum and The Freedom Trail. TD Garden and Museum ...

5/5Exceptional! (34 reviews)
Great weekend getaway

"The accommodations were awesome....clean, comfortable and convenient. Staying on the water was so relaxing and our kind of “social distancing”. Jon and Karen were fantastic hosts that felt more like old friends. Would highly recommend. We will be returning for sure."…"

Reviewed on 22 Mar 2021

Visit Boston on Green Turtle Houseboat in Boston Harbor! Plenty of Fresh Air
Beautiful Fort Hill 2 Bedroom 1 Bathroom

Beautiful Fort Hill 2 Bedroom 1 Bathroom

135 Cedar St, Boston, MA
The price is £151 per night from 3 May to 4 May

Located in Roxbury, this holiday home is within 2 miles (3 km) of Brigham and Women's Hospital, Boston Museum of Fine Arts and Dana-Farber Cancer Institute. ...

Beautiful Fort Hill 2 Bedroom 1 Bathroom
Boston Harbor Yacht,  AC/Heat, Walk to North End WiFi

Boston Harbor Yacht, AC/Heat, Walk to North End WiFi

13th St, Pier 8, Boston, MA

Located in Charlestown, this houseboat is within a 10-minute walk of The Freedom Trail and USS Constitution Museum. Boston Harbor and Bunker Hill Monument are ...

4.8/5Exceptional! (75 reviews)
Christmas on the Sea Pearl

"Celebrating Christmas 2020 aboard the Sea Pearl was a wonderful and memorable experience. Sherry met us at the gate to the marina when we arrived and oriented us to the surrounding sites and eateries. Having never stayed on a boat, we appreciated the safety tips and instructions she provided before ..."…"

Reviewed on 10 Jan 2021

Boston Harbor Yacht, AC/Heat, Walk to North End WiFi
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Winthrop you may be interested in

Winthrop Beach Inn and Suites

Winthrop Beach Inn and Suites

3 out of 5
312 Shirley Street, Winthrop, MA
The price is £81 per night from 17 Apr to 18 Apr
Winthrop Beach Inn and Suites
The Winthrop Arms Hotel And Restaurant

The Winthrop Arms Hotel And Restaurant

3 out of 5
130 Grovers Ave., Winthrop, MA
Free cancellationReserve now, pay when you stay
The price is £127 per night from 13 Apr to 14 Apr
The Winthrop Arms Hotel And Restaurant
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Holiday Apartments in Winthrop

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Frequently asked questions

Can I find a holiday rental in Winthrop?
Yes, we give you a choice of holiday rentals where you’ll be only 4 mi (6.5 km) from New England Aquarium, providing a more secluded option to escape the hustle and bustle. Visitors to Winthrop speak positively about the beaches and restaurants in this destination. Make sure you have time to check out the cafés and waterfront during your trip.
What are some of the best holiday rentals that Winthrop has to offer?
Waterfront One or Two Bedroom Private Apartment on Boston Harbor: This highly rated holiday home rental in Winthrop is located on the waterfront, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a hob. You and your friends and family can relax into your holiday with amenities such as a selection of games.
What can I see and do in Winthrop?
Winthrop Shore Reservation and Winthrop Beach are a couple of lovely local spots to get outside and enjoy nature. Other popular places to visit in the area include Black Falcon Cruise Terminal and Boston Harbor.
What are holiday rentals like in Winthrop?
Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winthrop. Holiday rentals feature amenities such as patios, hot tubs and fire pits so you’ll have all the comforts of home. If you’re concerned about a clean environment, a holiday rental can provide a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You’ll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for a family trip.