Winthrop Holiday Rentals

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Check prices for these dates

In two weeks
15 May - 17 May
In two months
26 Jun - 28 Jun
In three months
24 Jul - 26 Jul
In four months
21 Aug - 23 Aug

Our top choices for Winthrop holiday rentals

Interior

Casa de Los Clarey Boston Airport Beaches Off Street Parking Available

Casa de Los Clarey Boston Airport Beaches Off Street Parking Available
Winthrop
10.0 out of 10, Exceptional, (53 reviews)
"Loved the character of the property. Very roomy. Great location"
United States
Jeffrey V.
The price is HK$1,284
HK$2,607 total
includes taxes & fees
1 May - 2 May
Casa de Los Clarey Boston Airport Beaches Off Street Parking Available
Exterior

Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep

Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
Charlestown
9.8 out of 10, Exceptional, (201 reviews)
"Perfect host, perfect spot, WORTH EVERY PENNY "
Canada
Jennifer E.
The price is HK$1,191
HK$4,287 total
includes taxes & fees
4 May - 5 May
Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
Marina

"Travelers Choice Award" Spacious 2BD/2Bath Heat/AC 45 ft yacht Freedom Trail

"Travelers Choice Award" Spacious 2BD/2Bath Heat/AC 45 ft yacht Freedom Trail
Boston
10.0 out of 10, Exceptional, (121 reviews)
"Overall our stay was good!"
United States
Yan B.
The price is HK$2,659
HK$5,029 total
includes taxes & fees
12 May - 13 May
"Travelers Choice Award" Spacious 2BD/2Bath Heat/AC 45 ft yacht Freedom Trail
TV

Endless Summer: Oceanside Views

Endless Summer: Oceanside Views
Boston
10.0 out of 10, Exceptional, (42 reviews)
"Fun family adventure!"
United States
Jay
The price is HK$2,124
HK$3,773 total
includes taxes & fees
4 May - 5 May
Endless Summer: Oceanside Views
Rooftop terrace

Marriott Vacation Club® at Custom House, Boston

Marriott Vacation Club® at Custom House, Boston
3.5 star property
Downtown Boston
9.4 out of 10, Exceptional, (630 reviews)
"Beautiful hotel and easy access to everything."
United States
Kimberely
The price is HK$2,343
HK$2,694 total
includes taxes & fees
3 May - 4 May
Marriott Vacation Club® at Custom House, Boston
Living area

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.4 out of 10, Very good, (30 reviews)
"This was a perfect stay. Exactly how described. Highly recommend. "
United States
Yanmarie
The price is HK$1,509
HK$3,131 total
includes taxes & fees
3 May - 4 May
The Chester Hotel
Terrace/patio

Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,179 reviews)
"Excellent stay as always, my home away from home when traveling in the area."
United States
Sean
The price is HK$1,121
HK$1,252 total
includes taxes & fees
10 May - 11 May
Crescent Suites Hotel
1 bedroom, desk, laptop workspace, free WiFi

Furnished Apartments near Encore Boston

Furnished Apartments near Encore Boston
2.5 star property
Everett
8.6 out of 10, Excellent, (14 reviews)
"Nice spot"
United States
Kimberly
Furnished Apartments near Encore Boston
1 bedroom, desk, iron/ironing board, WiFi

Studio Awaits Your Next Stay!

Studio Awaits Your Next Stay!
Bay Village
9.2 out of 10, Wonderful, (5 reviews)
"Would stay again"
United States
mark p.
The price is HK$1,356
HK$2,412 total
includes taxes & fees
1 May - 2 May
Studio Awaits Your Next Stay!
Terrace/patio

Luxury 1 bedroom downtown appartment

Luxury 1 bedroom downtown appartment
Government Center
10.0 out of 10, Exceptional, (7 reviews)
"Gorgeous apartment with unmatched views. Dina is such a welcoming and gracious host and we had everything we needed. "
United States
Sarah D.
The price is HK$3,127
HK$4,621 total
includes taxes & fees
31 May - 1 Jun
Luxury 1 bedroom downtown appartment
Property grounds

Garden Studio, access to I-93 to Airport, Tufts U, Hiking & Chevalier Theater.

Garden Studio, access to I-93 to Airport, Tufts U, Hiking & Chevalier Theater.
Medford
10.0 out of 10, Exceptional, (55 reviews)
"Very cozy and comfortable rental, neighborhood was very nice and has plenty around it, great place to stay while traveling and enjoyed the stay, would recommend to anyone, hosts were also nice and very easy to communicate with."
United States
Tony V.
The price is HK$987
HK$2,110 total
includes taxes & fees
10 May - 11 May
Garden Studio, access to I-93 to Airport, Tufts U, Hiking & Chevalier Theater.
TV

Blissful South End Studio

Blissful South End Studio
Back Bay
10.0 out of 10, Exceptional, (2 reviews)
"Great place on a quiet street convenient to everything!"
United States
Penelope D.
The price is HK$870
HK$2,119 total
includes taxes & fees
18 May - 19 May
Blissful South End Studio
Living area

The Monty Boston

The Monty Boston
2.5 star property
Downtown Boston
9.6 out of 10, Exceptional, (36 reviews)
"Excellent location, very easy check in process, clean, just as the pictures showed online."
United States
shannon
The price is HK$4,394
HK$6,402 total
includes taxes & fees
1 May - 2 May
The Monty Boston
Fridge, microwave, oven, stovetop

3BR3Bth Entire House/Steps to Downtown & TD Garden

3BR3Bth Entire House/Steps to Downtown & TD Garden
North End
10.0 out of 10, Exceptional, (10 reviews)
"This place is so cool! Was incredibly clean, updated and offered all the amenities you need for a weekend get away. The location is wonderful as well with lots of markets, bakeries and restaurants all within walking distance. This is a must stay! "
United States
mary j.
The price is HK$2,116
HK$4,810 total
includes taxes & fees
17 May - 18 May
3BR3Bth Entire House/Steps to Downtown & TD Garden
Interior

Furnished Apts near Harvard Stadium

Furnished Apts near Harvard Stadium
2.0 star property
Allston
9.0 out of 10, Wonderful, (11 reviews)
"Great property. Very clean and spacious. Easy 15 minutes walk to Harvard. Easy check in and check out process"
United States
Tho
The price is HK$1,158
HK$2,232 total
includes taxes & fees
1 May - 2 May
Furnished Apts near Harvard Stadium
Dining

North End Entire House

North End Entire House
North End
10.0 out of 10, Exceptional, (21 reviews)
"Beautiful home in the heart of the north end. We had a wonderful stay!"
United States
Kerry y.
The price is HK$1,947
HK$4,616 total
includes taxes & fees
10 May - 11 May
North End Entire House
Exterior

Spacious 6 BR·7 Beds·3.5 BA house in charming Marblehead & Near Salem & Beaches

Spacious 6 BR·7 Beds·3.5 BA house in charming Marblehead & Near Salem & Beaches
marblehead
9.6 out of 10, Exceptional, (30 reviews)
"The host was very welcoming and the house was very comfortable for our large group"
United States
Shusmita D.
The price is HK$4,584
HK$8,350 total
includes taxes & fees
3 May - 4 May
Spacious 6 BR·7 Beds·3.5 BA house in charming Marblehead & Near Salem & Beaches
Private kitchen

3brm/1bath North End Gem

3brm/1bath North End Gem
North End
9.2 out of 10, Wonderful, (32 reviews)
"Perfect location"
United States
Scott P.
The price is HK$2,390
HK$5,018 total
includes taxes & fees
31 May - 1 Jun
3brm/1bath North End Gem
TV

Gorgeous Rare 3BR 3BA duplex with free Parking, Rare gorgeous 3 bds 3 baths w/ Parking in Best loca

Gorgeous Rare 3BR 3BA duplex with free Parking, Rare gorgeous 3 bds 3 baths w/ Parking in Best loca
North End
9.6 out of 10, Exceptional, (141 reviews)
"Charming apartment and perfectly appointed for our needs. The location was amazing. "
United States
Anne S.
The price is HK$4,937
HK$9,152 total
includes taxes & fees
19 May - 20 May
Gorgeous Rare 3BR 3BA duplex with free Parking, Rare gorgeous 3 bds 3 baths w/ Parking in Best loca
Smart TV, books

Bright 2BR by Boston Waterfront

Bright 2BR by Boston Waterfront
East Boston
10.0 out of 10, Exceptional, (25 reviews)
"Perfect place for a Boston get away. Hosts are extremely polite, very transparent about parking. Very conveniently located to be anywhere in the city quickly. Will be staying here again in the future"
United States
Blāk R.
The price is HK$924
HK$2,179 total
includes taxes & fees
5 May - 6 May
Bright 2BR by Boston Waterfront
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.
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Top Winthrop Hotel Reviews

The Revolution Hotel

The Revolution Hotel

10/10 Excellent
"Clean, very friendly and helpful. "
Steve 1-night trip
Posted 1 hour ago
The Revolution Hotel

Find out more about Winthrop

Search for holiday rentals in Winthrop on Expedia! You can easily find your home rentals, villas, holiday apartments in Winthrop using one of the methods below:

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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 3.7 mi (6 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?

Centrally located in the heart of Boston near T: This holiday home rental outside of Winthrop has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Winthrop?

With 5 Expedia holiday rentals, you're guaranteed to find just the right place for your Winthrop stay.

What can I see and do in Winthrop?

Winthrop Beach and Massachusetts Bay are a couple of lovely local spots to get outside and enjoy nature. Other popular places to visit in the area include Fenway Park 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.