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
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

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.
$469 nightly
The price is $524
Aug 10 - Aug 11
Total with taxes and fees
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.
$271 nightly
The price is $350
Aug 18 - Aug 19
Total with taxes and fees
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)
"7 min from the airport, seamless check in and entry and a spotless, welcoming place- with coffee! Great rental- perfect if you’re coming/going from Logan"
United States
Bridget
$333 nightly
The price is $383
Aug 10 - Aug 11
Total with taxes and fees
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.
$309 nightly
The price is $399
Aug 20 - Aug 21
Total with taxes and fees
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, (429 reviews)
"Great location so close to everything"
United States
Hunter
$172 nightly
The price is $198
Aug 10 - Aug 11
Total with taxes and fees
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
$267 nightly
The price is $307
Aug 10 - Aug 11
Total with taxes and fees
The Chester Hotel
Studio | Iron/ironing board, WiFi (free)

7. The Concord Hotel

The Concord Hotel
2.0 star property
South End
8.0 out of 10, Very Good, (7 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
$281 nightly
The price is $323
Aug 10 - Aug 11
Total with taxes and fees
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
$259 nightly
The price is $286
Aug 10 - Aug 11
Total with taxes and fees
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.
$217 nightly
The price is $280
Aug 10 - Aug 11
Total with taxes and fees
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.
$320 nightly
The price is $368
Aug 16 - Aug 17
Total with taxes and fees
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
$170 nightly
The price is $196
Aug 31 - Sep 1
Total with taxes and fees
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.
$243 nightly
The price is $313
Aug 9 - Aug 10
Total with taxes and fees
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.
$229 nightly
The price is $251
Aug 18 - Aug 19
Total with taxes and fees
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
$234 nightly
The price is $261
Aug 12 - Aug 13
Total with taxes and fees
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.
$246 nightly
The price is $289
Aug 10 - Aug 11
Total with taxes and fees
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.
$501 nightly
The price is $576
Aug 16 - Aug 17
Total with taxes and fees
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.
$763 nightly
The price is $875
Aug 11 - Aug 12
Total with taxes and fees
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
$246 nightly
The price is $289
Aug 10 - Aug 11
Total with taxes and fees
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
$356 nightly
The price is $459
Sep 2 - Sep 3
Total with taxes and fees
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)
"The accommodation is very good."
United States
honghao
$296 nightly
The price is $340
Aug 9 - Aug 10
Total with taxes and fees
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

Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

10/10 Excellent
"Nice location near fenway"
Mathieu 2-night trip
Posted 6 hours ago
Hyatt Regency Boston/Cambridge

Find out more about Winthrop

Everything you need to know about Winthrop vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winthrop vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winthrop vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winthrop vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winthrop. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winthrop in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $196 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winthrop rentals

At Expedia, we put the best Winthrop vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winthrop rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winthrop vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winthrop. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.