Winthrop Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

Check prices for these dates

In two weeks
Dec 5 - Dec 7
In two months
Jan 16 - Jan 18
In three months
Feb 13 - Feb 15
In four months
Mar 13 - Mar 15

Vacation Rentals in Winthrop

Exterior
Charming 1bedroom Apt with WiFi, AC in fabulous Winthrop Boston Airport Beaches

Charming 1bedroom Apt with WiFi, AC in fabulous Winthrop Boston Airport Beaches

Winthrop
9.8 out of 10, Exceptional, (6)
"Very good for the price, ideal location. Parking situation wasn't great, but otherwise was excellent."
United States
Ainsley S.
$169 nightly
The price is $189
Nov 19 - Nov 20
Total with taxes and fees
Charming 1bedroom Apt with WiFi, AC in fabulous Winthrop Boston Airport Beaches
Desk, laptop workspace, free WiFi, bed sheets
Bay Village Suites

Bay Village Suites

2.0 star property
Bay Village
6.4 out of 10, (244)
"Great location nice neighborhood "
United States
Jose
$168 nightly
The price is $193
Dec 1 - Dec 2
Total with taxes and fees
Bay Village Suites
Deluxe Studio | 1 bedroom, desk, iron/ironing board, free WiFi
Temple Place Suites

Temple Place Suites

2.5 star property
Downtown Boston
7.0 out of 10, Good, (316)
"Pretty clean room, good location, resonable price."
Canada
Beiyu
$178 nightly
The price is $205
Dec 1 - Dec 2
Total with taxes and fees
Temple Place Suites
42-inch TV with satellite channels
Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave

2.0 star property
South End
7.2 out of 10, Good, (130)
"I thoroughly enjoyed my stay. Great property in a nice neighborhood in Back Bay. Bonus: it's also near the Logan Express bus stop for easy airport access. "
United States
Mark
$188 nightly
The price is $216
Nov 19 - Nov 20
Total with taxes and fees
Maverick Suites at 400 Columbus Ave
Front of property
Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St

2.0 star property
Beacon Hill
7.6 out of 10, Good, (102)
"Great place to stay, in such a good location with everything you need nearby. Definitely recommend 😌"
United Kingdom
Jordan Elizabeth Marie
$199 nightly
The price is $229
Nov 30 - Dec 1
Total with taxes and fees
Maverick Suites at 40 Temple St
Exterior
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, (151)
"Good location, clean and quiet. Only thing that could be improved on would be luggage storage before check in "
United States
Kristee
$209 nightly
The price is $240
Nov 19 - Nov 20
Total with taxes and fees
Maverick Suites at 245 Newbury St
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, (245)
"Clean room, good location, check in check out easily!"
United States
HIEN T
$168 nightly
The price is $193
Dec 1 - Dec 2
Total with taxes and fees
Premier Suites - Bay Village
City Studio | 1 bedroom, Egyptian cotton sheets, premium bedding, memory foam beds
The Chester Hotel

The Chester Hotel

4.0 star property
South End
8.6 out of 10, Excellent, (27)
"The property was spacious and clean. We enjoyed our stay!"
United States
Bryan
$378 nightly
The price is $435
Nov 19 - Nov 20
Total with taxes and fees
The Chester Hotel
Deluxe Studio Suite (2nd Floor - Unit 202) | 1 bedroom, individually furnished, iron/ironing board, free WiFi
Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway

3.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (314)
"Spotless room, spotless building, great staff, comfortable bed. "
United States
Patricia
$199 nightly
The price is $229
Dec 3 - Dec 4
Total with taxes and fees
Maverick Suites at 28 Fenway
Lobby lounge
Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston

4.0 star property
Chinatown
8.0 out of 10, Very Good, (622)
"This unit and location was perfect for my trip! Super close to many of the attractions that we wanted to visit. "
United States
Lily
$200 nightly
The price is $230
Nov 26 - Nov 27
Total with taxes and fees
Global Luxury Suites Downtown Boston
Exterior
Best Location Studio In Downtown Boston

Best Location Studio In Downtown Boston

Downtown Boston
10.0 out of 10, Exceptional, (1)
"In town to celebrate a special event."
United States
Pam P.
$215 nightly
The price is $253
Dec 1 - Dec 2
Total with taxes and fees
Best Location Studio In Downtown Boston
1 bedroom, desk, WiFi, bed sheets
The Chester: Penthouse One Bedroom

The Chester: Penthouse One Bedroom

2.0 star property
South End
10.0 out of 10, Exceptional, (2)
"Absolutely loved my stay. Great location, beautiful place. Clean and bright. We will be back!"
United States
Linda C.
$375 nightly
The price is $430
Nov 25 - Nov 26
Total with taxes and fees
The Chester: Penthouse One Bedroom
Exterior
Amazing price & location w parking -North End -Boston

Amazing price & location w parking -North End -Boston

North End
9.6 out of 10, Exceptional, (58)
"Great location that was very convenient to all we wanted to do. "
United States
Jacob B.
$348 nightly
The price is $376
Nov 21 - Nov 22
Total with taxes and fees
Amazing price & location w parking -North End -Boston
1 bedroom, desk, iron/ironing board, WiFi
Studio Awaits Your Next Stay!

Studio Awaits Your Next Stay!

Bay Village
10.0 out of 10, Exceptional, (4)
"Would stay again"
United States
mark p.
$207 nightly
The price is $243
Nov 19 - Nov 20
Total with taxes and fees
Studio Awaits Your Next Stay!
Interior
Ideal North End 1brm Central To Everything

Ideal North End 1brm Central To Everything

North End
9.6 out of 10, Exceptional, (37)
"We had a very nice stay. Such a great location! Walkable to tons of restaurants and right near the Paul Revere statue and Old North Church!"
United States
Sean R.
Ideal North End 1brm Central To Everything
Marina
♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥

♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥

Marblehead
10.0 out of 10, Exceptional, (70)
"The property was in a great location and within walking distance of restaurants and activities. Would definitely stay here again."
United States
Pamela O.
$217 nightly
The price is $242
Dec 8 - Dec 9
Total with taxes and fees
♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥
Apartment | 1 bedroom, premium bedding, desk, iron/ironing board
Charlesgate Suites

Charlesgate Suites

3.5 star property
Fenway–Kenmore
9.4 out of 10, Exceptional, (199)
"New spot for us in South Bay. Convenient and easy with easy walk to Commonwealth and restaurants of Newbury"
United States
Brian
$368 nightly
The price is $423
Nov 30 - Dec 1
Total with taxes and fees
Charlesgate Suites
Smart TV, fireplace
NEW 2BR Historic Marblehead Home+Minutes to Beach

NEW 2BR Historic Marblehead Home+Minutes to Beach

2.0 star property
Marblehead
10.0 out of 10, Exceptional, (17)
"Enjoyed our stay. "
United States
Mary D.
$347 nightly
The price is $388
Dec 1 - Dec 2
Total with taxes and fees
NEW 2BR Historic Marblehead Home+Minutes to Beach
1 bedroom, desk, iron/ironing board, WiFi
Perfect One Bedroom Stay In Downtown Boston!

Perfect One Bedroom Stay In Downtown Boston!

Downtown Boston
8.6 out of 10, Excellent, (17)
"Temple Place Suites was a great place to stay for our few days in Boston. We loved being across from Boston Commons, near great bakerys and cafes. It was a comfortable apartment with great space and plenty of amenities. Staff was great at communicating about check in, building codes and check out. Wished there were dish towels and wash cloths. Otherwise, it was great!!"
United States
Christine
$220 nightly
The price is $258
Dec 1 - Dec 2
Total with taxes and fees
Perfect One Bedroom Stay In Downtown Boston!
Private kitchen
3brm/1bath North End Gem

3brm/1bath North End Gem

North End
9.2 out of 10, Wonderful, (27)
"Amazing location. Very responsive host"
United States
Sydney N.
$423 nightly
The price is $486
Dec 9 - Dec 10
Total with taxes and fees
3brm/1bath North End Gem
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winthrop Hotel Reviews

citizenM Boston Back Bay

citizenM Boston Back Bay

10/10 Excellent
"Excellent stay!"
Lindsey 3-night trip
Posted 6 hours ago
citizenM Boston Back Bay

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 $160 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?

Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston: This vacation home rental near Winthrop is located in the city center and has a patio, a selection of games, and air-conditioning to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Winthrop?

With 4 Expedia vacation rentals, you're sure to find just the right place for your Winthrop stay.

What can I see and do in Winthrop?

Boston Harbor Islands State Park 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 Fenway Park and Boston Harbor.

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.