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

Winthrop Vacation Rentals

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. Casa de Los Clarey • Boston • Logan • Beaches • Free Parking

Casa de Los Clarey • Boston • Logan • Beaches • Free Parking
Winthrop
10.0 out of 10, Exceptional, (57 reviews)
"Loved the character of the property. Very roomy. Great location"
United States
Jeffrey V.
$337 nightly
The price is $376
Sep 1 - Sep 2
Total with taxes and fees
Casa de Los Clarey • Boston • Logan • Beaches • Free Parking
Interior

2. 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
Interior

3. Beautiful 3-bedroom apartment with AC in welcoming Winthrop

Beautiful 3-bedroom apartment with AC in welcoming Winthrop
Winthrop
$349 nightly
The price is $389
Aug 23 - Aug 24
Total with taxes and fees
Beautiful 3-bedroom apartment with AC in welcoming Winthrop
Smart TV, books

4. 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
$269 nightly
The price is $309
Aug 10 - Aug 11
Total with taxes and fees
Bright 2BR by Boston Waterfront
Front of property

5. Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.0 star property
Beacon Hill
7.8 out of 10, Good, (141 reviews)
"Worth the stay"
Canada
Akansha
$232 nightly
The price is $267
Aug 12 - Aug 13
Total with taxes and fees
Maverick Suites at 40 Temple St
Rooftop terrace

6. Marriott Vacation Club® at Custom House, Boston

Marriott Vacation Club® at Custom House, Boston
3.5 star property
Downtown Boston
9.6 out of 10, Exceptional, (651 reviews)
"Best hotel for stay in Boston!"
United States
Frank
$305 nightly
The price is $351
Aug 30 - Aug 31
Total with taxes and fees
Marriott Vacation Club® at Custom House, Boston
Premium Apartment | Living area | 24-inch Smart TV with digital channels

7. 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
$247 nightly
The price is $284
Aug 9 - Aug 10
Total with taxes and fees
The Chester Hotel
1 Queen Bed with Sofa Bed (6th Floor - Elevator stops on 5th then stairs up) | Desk, iron/ironing board, WiFi (free), bed sheets

8. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.0 out of 10, Good, (433 reviews)
"Great location so close to everything"
United States
Hunter
$152 nightly
The price is $175
Aug 11 - Aug 12
Total with taxes and fees
Temple Place Suites
Exterior

9. Maverick Suites at 245 Newbury St

Maverick Suites at 245 Newbury St
2.0 star property
Back Bay
8.2 out of 10, Very Good, (197 reviews)
"Location was perfect! The room was great and exactly what I needed for my business trip"
United States
Michael
$246 nightly
The price is $283
Aug 9 - Aug 10
Total with taxes and fees
Maverick Suites at 245 Newbury St
Studio | Iron/ironing board, WiFi (free)

10. The Concord Hotel

The Concord Hotel
2.0 star property
South End
7.0 out of 10, Good, (10 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
$245 nightly
The price is $282
Aug 12 - Aug 13
Total with taxes and fees
The Concord Hotel
Lobby lounge

11. Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very Good, (733 reviews)
"Great property. Conveniently close to transit, shopping and Boston’s best districts."
United States
Neill
$313 nightly
The price is $359
Aug 25 - Aug 26
Total with taxes and fees
Global Luxury Suites Downtown Boston
42-inch TV with satellite channels

12. Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.4 out of 10, Good, (161 reviews)
"Well located"
United States
Evelyn
$229 nightly
The price is $253
Aug 24 - Aug 25
Total with taxes and fees
Maverick Suites at 400 Columbus Ave
Exterior

13. 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.
$280 nightly
The price is $361
Aug 20 - Aug 21
Total with taxes and fees
Walk everywhere - Seaport, North End, Beacon Hill. Steps from MBTA public transit. Keyless Entry!
1 bedroom, iron/ironing board, WiFi, bed sheets

14. Primo North End Studio

Primo North End Studio
North End
9.4 out of 10, Exceptional, (19 reviews)
"Great place, amazing location!"
United States
Christopher W.
$309 nightly
The price is $355
Aug 16 - Aug 17
Total with taxes and fees
Primo North End Studio
TV

15. Prime Central 1brm in North End Boston

Prime Central 1brm in North End Boston
North End
9.6 out of 10, Exceptional, (27 reviews)
"Excellent location, wonderful unit! "
United States
Mary M.
$406 nightly
The price is $467
Aug 14 - Aug 15
Total with taxes and fees
Prime Central 1brm in North End Boston
Deluxe Double Room, Shared Bathroom | Iron/ironing board, WiFi (free), bed sheets

16. Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.2 out of 10, (319 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
$154 nightly
The price is $177
Aug 9 - Aug 10
Total with taxes and fees
Premier Suites - Bay Village
Exterior

17. Light-filled Studio | Back Bay

Light-filled Studio | Back Bay
Back Bay
9.6 out of 10, Exceptional, (9 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.
$195 nightly
The price is $251
Aug 10 - Aug 11
Total with taxes and fees
Light-filled Studio | Back Bay
1 bedroom, desk, iron/ironing board, internet

18. Cozy Studio Steps from Boston Common and Theaters

Cozy Studio Steps from Boston Common and Theaters
Bay Village
7.6 out of 10, Good, (15 reviews)
"All good, would definitely stay again"
United States
Dan C.
$228 nightly
The price is $268
Aug 11 - Aug 12
Total with taxes and fees
Cozy Studio Steps from Boston Common and Theaters
Indoor pool, pool umbrellas, sun loungers

19. Global Luxury Suites East Boston

Global Luxury Suites East Boston
4.0 star property
East Boston
6.8 out of 10, (202 reviews)
"Perfect location, professional staff, great parking arrangement "
United States
Joli
$307 nightly
The price is $353
Sep 6 - Sep 7
Total with taxes and fees
Global Luxury Suites East Boston
Front of property

20. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (402 reviews)
"Easy to move-in, location is good for traveler. The shower room not that clean, some hair from previous guests, just clean it can be manage by guest."
Taiwan
LICHIEH
$237 nightly
The price is $273
Aug 11 - Aug 12
Total with taxes and fees
Maverick Suites at 28 Fenway
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

Doubletree By Hilton Boston Logan Airport Chelsea

Doubletree By Hilton Boston Logan Airport Chelsea

10/10 Excellent
"It was a great stay comfy beds and nice and cool on the hot days we spent in the city"
Christian 3-night trip
Posted less than an hour ago
Doubletree By Hilton Boston Logan Airport Chelsea

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 $175 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 Donovan 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.