Winthrop Vacation Rentals from ￥28,865: Search Short-Term Rentals

Q: What are some of the best vacation home rentals in Winthrop?

Cozy 3BD 1BA near Beach T-10 Min from Boston : This vacation home rental near Winthrop is equipped with a patio, free WiFi, and a Smart TV to help you feel comfortable during your stay. 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.

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Our top choices for Winthrop vacation rentals

Casa de Los Clarey Boston Airport Beaches Off Street Parking Available

Winthrop

Jeffrey V.

￥61,548 total

includes taxes & fees

Jun 11 - Jun 12

Marriott Vacation Club® at Custom House, Boston

Downtown Boston

Noelle

￥59,402 total

includes taxes & fees

Jul 6 - Jul 7

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

The Chester Hotel

South End

Mary

￥49,785 total

includes taxes & fees

Jun 11 - Jun 12

Village Colonial / Harbor Views.

Cohasset

Melissa I.

￥109,809 total

includes taxes & fees

Jun 16 - Jun 17

3BR3Bth Entire House/Steps to Downtown & TD Garden

North End

mary j.

￥99,020 total

includes taxes & fees

Jun 21 - Jun 22

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

Fenway–Kenmore

Jan

￥49,870 total

includes taxes & fees

Jun 13 - Jun 14

Luxury and Modern Apt near Mall/ Hospital

Danvers

Cailey Faye S.

￥63,609 total

includes taxes & fees

Jun 21 - Jun 22

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

Wilmington

￥102,000 total

includes taxes & fees

Jun 12 - Jun 13

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Top Winthrop Hotel Reviews

The Dagny Boston

10/10 Excellent

"The location was excellent, very clean and nicely decorated rooms."

The Westin Boston Seaport District

2/10 Terrible

"This is a large, bland corporate hotel. Food is tasteless, background music sounds like it’s AI-generated and you can’t escape it. Beds a little saggy. And their pricing algorithm tries to squeeze as much out of you as possible. But the staff are genuinely nice and helpful."

Hilton Boston Logan Airport

10/10 Excellent

"We had a great stay at the Hilton Logan Airport Hotel. The rooms were spacious, clean, and very comfortable, especially the bed which made for a great night’s sleep. The staff was extremely helpful and friendly throughout our stay. Overall, a very convenient and pleasant experience near the airport. We would definitely stay here again!"

The Revolution Hotel

2/10 Terrible

"I had stayed before and liked the vibe. When I checked in the hotel had oversold the rooms and the front desk criticized me for using hotel.com and not Expedia or bookings. They found a room for me that wasn’t what I had reserved and that was fine. The staff told me if I wanted that room I had to make the reservation directly through hotel and I would have to deal with getting the refund from hotels.com myself. it took 45 min to Check in, and I felt like I was on trail in a courthouse."

citizenM Boston Back Bay

10/10 Excellent

"Staying at Citizen M is a lot like shopping at Aldi. There's some insider knowledge needed. The hotel is fairly high tech. The check in is mostly self service. You even make your own key card. You must use your key card to operate the elevator, which is great for security, but frustrating for first time travelers who aren't in on the secret. In your room, you use an ipad to operate your TV, lights, climate, and blinds. The room is small, but the lobby is huge and really nice — the kind of place you'll enjoy hanging in. There's a nice outdoor patio, too. Overall, I enjoyed the experience and plan on returning. My only complaints: 1) No water glasses in the rooms (a complication for taking pills) 2) After checkout, you can hang in the lobby but can't use the outdoor patio because it requires a keycard."

Find out more about Winthrop

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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?

Cozy 3BD 1BA near Beach T-10 Min from Boston: This vacation home rental near Winthrop is equipped with a patio, free WiFi, and a Smart TV to help you feel comfortable during your stay. 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 5 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 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.

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Check prices for these dates

Our top choices for Winthrop vacation rentals

Casa de Los Clarey Boston Airport Beaches Off Street Parking Available

Marriott Vacation Club® at Custom House, Boston

The Chester Hotel

Village Colonial / Harbor Views.

3BR3Bth Entire House/Steps to Downtown & TD Garden

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

Luxury and Modern Apt near Mall/ Hospital

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

Bright & Stylish Coastal Retreat in Marblehead Historic Center w Parking!

Central Salem Retreat 2bd W/ parking

Boston 2bd King Bed near Harvard, MIT, subway near Boston. On-site free Parking

Prime Central 1brm in North End Boston

Sailors Aweigh: Marblehead 3BR Retreat with Outdoor Space Near Harbor & Beaches

Global Luxury Suites Downtown Boston

Stylish Back Bay Retreat, Steps from Prudential

Lux 1st floor 3brm/1bath North End

The widow’s walk your very own spa experience

Garden Studio, access to I-93 to Airport, Tufts U, Hiking & Chevalier Theater.

Crescent Suites Hotel

Cozy Modern 2 Bedrooms Apartment Close to Boston

Find vacation rentals that suit your style

Top Winthrop Hotel Reviews

The Dagny Boston

The Midtown Hotel MOD Collection by Sonesta

Harborside Inn Of Boston

The Westin Boston Seaport District

Hilton Boston Logan Airport

Hyatt Regency Boston

The Revolution Hotel

Sheraton Boston, a Marriott Hotel

citizenM Boston Back Bay

Find out more about Winthrop

Frequently asked questions

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