Winthrop Vacation Rentals from $174: Search Short-Term Rentals

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Our top choices for Winthrop vacation rentals

1. Private 1BR Top-Floor Retreat • Free Parking • Boston, Logan & Beaches

Winthrop

Kristie P.

$183 nightly

Sep 16 - Sep 17

Total with taxes and fees

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

Winthrop

Jeffrey V.

$336 nightly

Sep 1 - Sep 2

Total with taxes and fees

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

Winthrop

$309 nightly

Aug 26 - Aug 27

Total with taxes and fees

4. Marriott Vacation Club® at Custom House, Boston

Downtown Boston

Brittany

$263 nightly

Aug 30 - Aug 31

Total with taxes and fees

5. Bright 2BR by Boston Waterfront

East Boston

Bridget

$279 nightly

Aug 28 - Aug 29

Total with taxes and fees

1 Queen Bed with Sofa Bed (6th Floor - Elevator stops on 5th then stairs up) | Desk, iron/ironing board, WiFi (free), bed sheets

6. Temple Place Suites

Downtown Boston

Hunter

$151 nightly

Aug 31 - Sep 1

Total with taxes and fees

7. Maverick Suites at 40 Temple St

Beacon Hill

Akansha

$236 nightly

Aug 30 - Aug 31

Total with taxes and fees

Deluxe Double Room, Shared Bathroom | Iron/ironing board, WiFi (free), bed sheets

8. Premier Suites - Bay Village

Bay Village

Obianuju

$154 nightly

Aug 27 - Aug 28

Total with taxes and fees

Studio | Iron/ironing board, WiFi (free)

9. The Concord Hotel

South End

Cotie

$284 nightly

Aug 26 - Aug 27

Total with taxes and fees

10. Perfetto North End 1brm

North End

Deborah S.

$324 nightly

Aug 27 - Aug 28

Total with taxes and fees

11. Global Luxury Suites Downtown Boston

Chinatown

afshin

$311 nightly

Aug 27 - Aug 28

Total with taxes and fees

Premium Apartment | Living area | 24-inch Smart TV with digital channels

12. The Chester Hotel

South End

Shanida

$328 nightly

Aug 26 - Aug 27

Total with taxes and fees

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

Downtown Boston

Rachael M.

$310 nightly

Aug 26 - Aug 27

Total with taxes and fees

14. Maverick Suites at 245 Newbury St

Back Bay

lane

$246 nightly

Aug 31 - Sep 1

Total with taxes and fees

15. Maverick Suites at 400 Columbus Ave

South End

Evelyn

$244 nightly

Aug 26 - Aug 27

Total with taxes and fees

16. Sleek Studio Apartment in the South End

Back Bay

Unspecified U.

$237 nightly

Aug 26 - Aug 27

Total with taxes and fees

17. Modern North End Studio

North End

James

$360 nightly

Sep 6 - Sep 7

Total with taxes and fees

18. Maverick Suites at 28 Fenway

Fenway–Kenmore

LICHIEH

$236 nightly

Aug 27 - Aug 28

Total with taxes and fees

Coffee/tea maker, fridge, microwave, oven

19. 3BR3Bth Entire House/Steps to Downtown & TD Garden

North End

Erin A.

$476 nightly

Aug 26 - Aug 27

Total with taxes and fees

1 bedroom, desk, iron/ironing board, WiFi

20. Perfect One Bedroom Stay In Downtown Boston!

Downtown Boston

Keith

$221 nightly

Sep 1 - Sep 2

Total with taxes and fees

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Top Winthrop Hotel Reviews

Omni Boston Hotel at the Seaport

10/10 Excellent

"Great location. Excellent amenities. Loved the coffee shop."

citizenM Boston Back Bay

10/10 Excellent

"Note I have stated at the Washington, DC location. That’s why I picked this location. Great location, across street from T, stop st top of Newbury Street, short walk to Fenway Park (and the Art Museums), - I thought it was a good deal for breakfast. - gym was nice and clean. - I m 70 and not particularly good with electronics, but I had no problem using the TV. (I didn’t view the preview, I should have done so, I’m sure it would have been helpful)"

Doubletree By Hilton Boston Logan Airport Chelsea

8/10 Good

"Wonderful hotel stay! Amazing staff about 20 minutes from the Boston convention center where I was! My only warning to people is that if you do choose this hotel know that it’s literally right across the street from a train station so at 3 AM 4 AM I was hearing the train go off from my hotel room when trying to sleep 😅😓"

The Godfrey Hotel Boston

10/10 Excellent

"We had 4 rooms combined and from the moment we stepped into the Godfrey we were treated wonderfully. The hotel itself was neat and clean, the staff were eager to help and super friendly. The rooms were very clean and comfortable. The coffee shop downstairs was icing on the cake! I would definitely recommend staying at the Godfrey!"

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 $174 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.

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Things to do in 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?

Boston's Best Vacation Home : This vacation home near Winthrop is equipped with a fireplace, air-conditioning, and laundry facilities to help you feel comfortable during your stay.

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 Massachusetts Bay 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.

Winthrop Vacation Rentals

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Check prices for these dates

Our top choices for Winthrop vacation rentals

1. Private 1BR Top-Floor Retreat • Free Parking • Boston, Logan & Beaches

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

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

4. Marriott Vacation Club® at Custom House, Boston

5. Bright 2BR by Boston Waterfront

6. Temple Place Suites

7. Maverick Suites at 40 Temple St

8. Premier Suites - Bay Village

9. The Concord Hotel

10. Perfetto North End 1brm

11. Global Luxury Suites Downtown Boston

12. The Chester Hotel

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

14. Maverick Suites at 245 Newbury St

15. Maverick Suites at 400 Columbus Ave

16. Sleek Studio Apartment in the South End

17. Modern North End Studio

18. Maverick Suites at 28 Fenway

19. 3BR3Bth Entire House/Steps to Downtown & TD Garden

20. Perfect One Bedroom Stay In Downtown Boston!

Find vacation rentals that suit your style

Top Winthrop Hotel Reviews

Omni Boston Hotel at the Seaport

Find out more about Winthrop

Explore a world of travel with Expedia

Frequently asked questions

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