Winthrop-Boston

Winthrop Vacation Rentals

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Check prices for these dates

In two weeks
Jul 3 - Jul 5
In two months
Aug 14 - Aug 16
In three months
Sep 11 - Sep 13
In four months
Oct 9 - Oct 11

Our top choices for Winthrop vacation 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, (55 reviews)
"Loved the character of the property. Very roomy. Great location"
United States
Jeffrey V.
$281 nightly
The price is $314
Jun 18 - Jun 19
Total with taxes and fees
Casa de Los Clarey Boston Airport Beaches Off Street Parking Available
Interior

Fun houseboat. Walk to Boston attractions WIFI

Fun houseboat. Walk to Boston attractions WIFI
Boston
9.8 out of 10, Exceptional, (96 reviews)
"Great location, very clean, very safe, beautiful view of the city when walking. Definitely would recommend ~"
United States
Tracey
$523 nightly
The price is $553
Jun 21 - Jun 22
Total with taxes and fees
Fun houseboat. Walk to Boston attractions WIFI
Interior

Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino

Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino
Chelsea
9.4 out of 10, Exceptional, (105 reviews)
"host was so welcoming and we enjoyed they stay"
United States
Roshawn D.
$613 nightly
The price is $685
Jul 1 - Jul 2
Total with taxes and fees
Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino
1 Queen Bed with Sofa Bed (6th Floor - Elevator stops on 5th then stairs up) | Desk, iron/ironing board, free WiFi, bed sheets

Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.0 out of 10, Good, (390 reviews)
"Wonderful stay at this property. Location was excellent, and the host is very quick and responsive to answer any questions you may have."
United States
Jennifer
$188 nightly
The price is $216
Jun 24 - Jun 25
Total with taxes and fees
Temple Place Suites
Suite (Luxury 1BR w/ King Bed & City Views) | Egyptian cotton sheets, premium bedding, down comforters

Symple Live

Symple Live
4.5 star property
Fenway–Kenmore
8.0 out of 10, Very Good, (2 reviews)
"The property was great, aside from very busy outside streets, which made it difficult to sleep, but was not the fault of the host."
United States
Nicholas
$295 nightly
The price is $339
Jun 24 - Jun 25
Total with taxes and fees
Symple Live
1 bedroom, desk, iron/ironing board, WiFi

Studio Awaits Your Next Stay!

Studio Awaits Your Next Stay!
Bay Village
8.4 out of 10, Very Good, (6 reviews)
"Would stay again"
United States
mark p.
$238 nightly
The price is $280
Jun 21 - Jun 22
Total with taxes and fees
Studio Awaits Your Next Stay!
Interior

Enjoyable 2-bedroom lower level apartment in charming Lynn

Enjoyable 2-bedroom lower level apartment in charming Lynn
Lynn
9.6 out of 10, Exceptional, (10 reviews)
$243 nightly
The price is $267
Jul 7 - Jul 8
Total with taxes and fees
Enjoyable 2-bedroom lower level apartment in charming Lynn
Desk, iron/ironing board, WiFi, bed sheets

Bright 1 Bedroom | Downtown Boston

Bright 1 Bedroom | Downtown Boston
Bay Village
10.0 out of 10, Exceptional, (1 review)
"Great location to explore Boston with your dogs"
Canada
Thiery
$240 nightly
The price is $309
Jul 6 - Jul 7
Total with taxes and fees
Bright 1 Bedroom | Downtown Boston
Deluxe Double Room, Shared Bathroom | Iron/ironing board, free WiFi, bed sheets

Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.2 out of 10, (291 reviews)
"Great location and well maintained"
United States
EDDIE
$176 nightly
The price is $202
Jun 24 - Jun 25
Total with taxes and fees
Premier Suites - Bay Village
Exterior

Light-filled Studio | Back Bay

Light-filled Studio | Back Bay
Back Bay
10.0 out of 10, Exceptional, (2 reviews)
"It was a great stay!"
United States
Adina S.
$196 nightly
The price is $253
Jul 6 - Jul 7
Total with taxes and fees
Light-filled Studio | Back Bay
Exterior

Awesome downtown location - walking distance to great restaurants, Boston Common, Southie + Seaport

Awesome downtown location - walking distance to great restaurants, Boston Common, Southie + Seaport
Downtown Boston
9.4 out of 10, Exceptional, (3 reviews)
"Location was awesome and central to the attractions. "
United States
Shelly B.
$433 nightly
The price is $558
Jul 14 - Jul 15
Total with taxes and fees
Awesome downtown location - walking distance to great restaurants, Boston Common, Southie + Seaport
Iron/ironing board, free WiFi

The Concord Hotel

The Concord Hotel
2.0 star property
South End
$287 nightly
The price is $330
Jun 30 - Jul 1
Total with taxes and fees
The Concord Hotel
1 bedroom, iron/ironing board, WiFi, bed sheets

Primo North End Studio

Primo North End Studio
North End
9.2 out of 10, Wonderful, (15 reviews)
"Great place, amazing location!"
United States
Christopher W.
$360 nightly
The price is $414
Jul 15 - Jul 16
Total with taxes and fees
Primo North End Studio
Outdoor dining

🎖The Boiler Room - Close to Subway & Downtown🎖

🎖The Boiler Room - Close to Subway & Downtown🎖
Dorchester
9.8 out of 10, Exceptional, (82 reviews)
"Host was amazing and responded right away with any questions or concerns we had! Beautiful place to stay!"
United States
Amy I.
$319 nightly
The price is $367
Jul 14 - Jul 15
Total with taxes and fees
🎖The Boiler Room - Close to Subway & Downtown🎖
TV

Beautiful 1BR near Fenway Park + Kenmore!

Beautiful 1BR near Fenway Park + Kenmore!
Fenway–Kenmore
$270 nightly
The price is $348
Jun 21 - Jun 22
Total with taxes and fees
Beautiful 1BR near Fenway Park + Kenmore!
Exterior

Stylish Back Bay Retreat, Steps from Prudential

Stylish Back Bay Retreat, Steps from Prudential
Back Bay
8.8 out of 10, Excellent, (11 reviews)
"Excellent location for restaurants, shops, sightseeing. Lovely buzz around the area, with park & river close by to escape if necessary. Large lounge area to put your feet up between trips, and adequate glasses etc for drinks and nibbles between the treats at the bakeries and restaurants nearby."
United Kingdom
Jude
$389 nightly
The price is $418
Jul 1 - Jul 2
Total with taxes and fees
Stylish Back Bay Retreat, Steps from Prudential
Exterior

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

Free Parking at 1 Bed Basement Apt, Near BU & MIT
Fenway–Kenmore
8.4 out of 10, Very Good, (23 reviews)
"Friendly hosts"
United States
Jan
$299 nightly
The price is $332
Jun 30 - Jul 1
Total with taxes and fees
Free Parking at 1 Bed Basement Apt, Near BU & MIT
TV, books

Just Ducky: Lake Front, Easy Access to Boston, Mobility Friendly

Just Ducky: Lake Front, Easy Access to Boston, Mobility Friendly
Wilmington
$561 nightly
The price is $616
Jun 30 - Jul 1
Total with taxes and fees
Just Ducky: Lake Front, Easy Access to Boston, Mobility Friendly
Living area

On River/Harvard Sq. two blocks

On River/Harvard Sq. two blocks
West Cambridge
8.0 out of 10, Very Good, (44 reviews)
"Very convenient for our stay with a grandson attending Harvard"
United States
Christy
$274 nightly
The price is $314
Jun 30 - Jul 1
Total with taxes and fees
On River/Harvard Sq. two blocks
Premium Apartment | Living area | 24-inch Smart TV with digital channels

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.6 out of 10, Excellent, (33 reviews)
"Charming room, fresh towels, clean!! I would stay here again."
United States
Mary
$270 nightly
The price is $310
Jun 30 - Jul 1
Total with taxes and fees
The Chester Hotel
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 Dagny Boston

The Dagny Boston

8/10 Good
"Great location, close to harbor and walkabe to The Common. Big rooms, spotless, brilliant staff ( all of them). Need a late night pizza ? See the concierge, top guy. Central but v quiet. A few Irish bars close by, loved Dooley's , just down the street. Not close to subway - if you need it, I didn't."
Gavin 3-night trip
Posted less than an hour ago
The Dagny Boston

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 $142 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?

Boston's Best Vacation Home : This vacation home rental 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?

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