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

Winthrop Vacation Rentals

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Check prices for these dates

In two weeks
14 Aug - 16 Aug
In two months
25 Sep - 27 Sep
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Winthrop vacation rentals

Interior

1. Spectacular Oceanfront 1 Bedroom Unit in Winthrop

Spectacular Oceanfront 1 Bedroom Unit in Winthrop
Winthrop
9.8 out of 10, Exceptional, (26 reviews)
"This beach front stay made our girl's city trip so much more special.Excellent communication, very clean, and it had everything we needed and more. "
United States
Katie S.
The price is AED 1,286
AED 2,088 total
includes taxes & fees
10 Aug - 11 Aug
Spectacular Oceanfront 1 Bedroom Unit in Winthrop
1 bedroom, desk, iron/ironing board, WiFi

2. Downtown Studio | Students Welcome | W/D in unit

Downtown Studio | Students Welcome | W/D in unit
Downtown Boston
9.4 out of 10, Exceptional, (3 reviews)
"Was worth the price all around"
United States
steven l.
The price is AED 485
AED 1,284 total
includes taxes & fees
18 Aug - 19 Aug
Downtown Studio | Students Welcome | W/D in unit
Smart TV, books

3. Bright 2BR by Boston Waterfront

Bright 2BR by Boston Waterfront
East Boston
9.6 out of 10, Exceptional, (40 reviews)
"We had a wonderful stay. The place was clean, well-equipped, and had everything we needed for a comfortable visit. Communication with the hosts was excellent—they were responsive, friendly, and very helpful throughout our stay."
United States
Jami E.
The price is AED 702
AED 1,576 total
includes taxes & fees
24 Aug - 25 Aug
Bright 2BR by Boston Waterfront
Exterior

4. Walk everywhere - Seaport, North End, Beacon Hill. Steps from MBTA public transit. Keyless Entry!

Walk everywhere - Seaport, North End, Beacon Hill. Steps from MBTA public transit. Keyless Entry!
Downtown Boston
9.0 out of 10, Wonderful, (2 reviews)
"Host was very communicative. The apartment was very clean and spacious and the location was fantastic! A lot of things in walking distance and train stop nearby for getting to other parts of the city was convenient. I would highly recommend this host and their space! Thank you for your hospitality! Would love to come back."
United States
Rachael M.
The price is AED 607
AED 1,465 total
includes taxes & fees
20 Aug - 21 Aug
Walk everywhere - Seaport, North End, Beacon Hill. Steps from MBTA public transit. Keyless Entry!
1 Queen Bed with Sofa Bed (6th Floor - Elevator stops on 5th then stairs up) | Desk, iron/ironing board, WiFi (free), bed sheets

5. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.0 out of 10, Good, (427 reviews)
"Great location so close to everything"
United States
Hunter
The price is AED 443
AED 741 total
includes taxes & fees
6 Aug - 7 Aug
Temple Place Suites
Premium Apartment | Living area | 24-inch Smart TV with digital channels

6. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (36 reviews)
"It was in a great neighbourhood and beautiful decorated"
United Kingdom
Shanida
The price is AED 588
AED 1,141 total
includes taxes & fees
3 Aug - 4 Aug
The Chester Hotel
Studio | Iron/ironing board, WiFi (free)

7. The Concord Hotel

The Concord Hotel
2.0 star property
South End
7.8 out of 10, Good, (6 reviews)
"Clean room and linens, great location and comfortable bed. Only complaint is the street noise and sounds from residents in upstairs apartment which was kind of loud. All things considered I’d stay again as it was a good value spot"
United States
Nancy
The price is AED 565
AED 1,114 total
includes taxes & fees
3 Aug - 4 Aug
The Concord Hotel
Exterior

8. Free Parking at 1 Bed Basement Apt, Near BU & MIT

Free Parking at 1 Bed Basement Apt, Near BU & MIT
Fenway–Kenmore
8.6 out of 10, Excellent, (27 reviews)
"Friendly hosts"
United States
Jan
The price is AED 349
AED 801 total
includes taxes & fees
3 Aug - 4 Aug
Free Parking at 1 Bed Basement Apt, Near BU & MIT
Exterior

9. Light-filled Studio | Back Bay

Light-filled Studio | Back Bay
Back Bay
9.6 out of 10, Exceptional, (8 reviews)
"Perfect location! On a quiet street right in the heart of the Back Bay. Can easily walk to restaurants, grocery stores, the Prudential Center, and pubic transportation. Close to the nearby colleges which was helpful for our stay. We were able to support our college-age kid through a tough moment. It was clean, comfortable, and management was responsive and friendly. It was easy in and out. We’ll definitely come back. This would be perfect if you had any kind of medical emergency or needed to...
United States
Gretchen J.
The price is AED 492
AED 1,213 total
includes taxes & fees
30 Aug - 31 Aug
Light-filled Studio | Back Bay
1 bedroom, iron/ironing board, WiFi, bed sheets

10. Primo North End Studio

Primo North End Studio
North End
9.4 out of 10, Exceptional, (18 reviews)
"Great place, amazing location!"
United States
Christopher W.
The price is AED 606
AED 1,351 total
includes taxes & fees
16 Aug - 17 Aug
Primo North End Studio
Deluxe Double Room, Shared Bathroom | Iron/ironing board, WiFi (free), bed sheets

11. Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.2 out of 10, (316 reviews)
"Lovely small property with thoughtful touches like cool water bottles & Nespresso available 24hrs. I had to take a last minute Zoom call and the front desk reserved the business center room for me. The rooms themselves are a bit small but very comfortable beds and linens."
United States
Theresa
The price is AED 414
AED 666 total
includes taxes & fees
31 Aug - 1 Sep
Premier Suites - Bay Village
Exterior

12. Blissful South End Studio

Blissful South End Studio
Back Bay
9.6 out of 10, Exceptional, (5 reviews)
"Great place on a quiet street convenient to everything!"
United States
Penelope D.
The price is AED 459
AED 1,165 total
includes taxes & fees
9 Aug - 10 Aug
Blissful South End Studio
Interior

13. Enjoyable 2-bedroom lower level apartment in charming Lynn

Enjoyable 2-bedroom lower level apartment in charming Lynn
Lynn
9.0 out of 10, Wonderful, (17 reviews)
"Easy, clean and a comfortable stay"
United States
Justin P.
The price is AED 477
AED 899 total
includes taxes & fees
18 Aug - 19 Aug
Enjoyable 2-bedroom lower level apartment in charming Lynn
Property grounds

14. 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, (62 reviews)
"Owner accessible, and cleanliness and convenience was very good."
United States
Ian
The price is AED 440
AED 963 total
includes taxes & fees
24 Aug - 25 Aug
Garden Studio, access to I-93 to Airport, Tufts U, Hiking & Chevalier Theater.
TV, offices

15. Studio in the Heart of Boston!

Studio in the Heart of Boston!
Downtown Boston
10.0 out of 10, Exceptional, (2 reviews)
"My stay was excellent! One of the best parts was how responsive the property management team was to communicate with me so quickly on the VRBO app."
United States
Landon W.
The price is AED 577
AED 1,061 total
includes taxes & fees
3 Aug - 4 Aug
Studio in the Heart of Boston!
Interior

16. Fun houseboat. Walk to Boston attractions WIFI

Fun houseboat. Walk to Boston attractions WIFI
Boston
9.8 out of 10, Exceptional, (101 reviews)
"Beautiful place! Lots to do!"
United States
Julieann D.
The price is AED 680
AED 2,023 total
includes taxes & fees
16 Aug - 17 Aug
Fun houseboat. Walk to Boston attractions WIFI
Interior

17. Upscale Central 2BR Condo with Gym & Parking near Boston Common, MGH & TUFTS!

Upscale Central 2BR Condo with Gym & Parking near Boston Common, MGH & TUFTS!
Bay Village
10.0 out of 10, Exceptional, (1 review)
"Stayed here for two nights. Everything was great. Room was convenient to everything in Boston and the check in and out went smooth. Owner even called to check if everything was ok. Definitely would recommend. "
United States
Matthew B.
The price is AED 1,120
AED 3,143 total
includes taxes & fees
16 Aug - 17 Aug
Upscale Central 2BR Condo with Gym & Parking near Boston Common, MGH & TUFTS!
1 bedroom, desk, iron/ironing board, WiFi

18. Perfect One Bedroom Stay In Downtown Boston!

Perfect One Bedroom Stay In Downtown Boston!
Downtown Boston
8.4 out of 10, Very Good, (21 reviews)
"Very easy check in, great location to walk to the ballet. Tons of great bars around"
United States
Keith
The price is AED 577
AED 1,061 total
includes taxes & fees
3 Aug - 4 Aug
Perfect One Bedroom Stay In Downtown Boston!
TV

19. Boston Financial District 1BR | Walk to anything!

Boston Financial District 1BR | Walk to anything!
Downtown Boston
10.0 out of 10, Exceptional, (1 review)
"The room was great, for what little time we spent in it, it was a really cozy place. The bed was huge, and really comfortable, I loved how much light the place got as well, with the windows. We were slightly off put by the pictures of the place with how incredibly beige the place looked, but I can assure you it looks way better in person lol. The location is great as well, I've never been to a city this walkable, so I'm glad we picked somewhere right in the middle of it, almost every direction...
United States
Kyle
The price is AED 764
AED 1,696 total
includes taxes & fees
13 Aug - 14 Aug
Boston Financial District 1BR | Walk to anything!
Lobby lounge

20. Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very Good, (729 reviews)
"Great property. Conveniently close to transit, shopping and Boston’s best districts."
United States
Neill
The price is AED 652
AED 1,191 total
includes taxes & fees
16 Aug - 17 Aug
Global Luxury Suites Downtown Boston
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

Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

10/10 Excellent
"Check in and out was easy on my phone. Room was clean quiet and close to where we had events and I would stay there again for in the future."
Robert M 1-night trip
Posted less than an hour ago
Club Quarters Hotel Faneuil Hall, Boston

Frequently asked questions

Can I find a vacation rental in Winthrop?

Yes, we offer vacation rentals where you'll be only 3.7 mi (6 km) from New England Aquarium, giving you 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 cafes and waterfront during your trip.

What are some of the best vacation home rentals in Winthrop?

Steps from the ocean minutes from Boston Beach house for rent 10% off first week: Visitors like this Winthrop vacation home rental. It is located near the beach and offers a selection of books, 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 fridge, a stovetop, and a microwave, so you can cook with friends or family.

How many vacation rentals are there in Winthrop?

With 6 Expedia vacation rentals, you're sure to find just the right place for your Winthrop stay.

What can I see and do in Winthrop?

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

What are vacation rentals like in Winthrop?

Vacation rentals are privately owned properties you can stay in for a couple days or more in Winthrop. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so you'll have everything you need. If you're concerned about cleanliness, a vacation rental can provide a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great choice for families.