Winthrop Vacation Rentals from CA $100: Short-Term Rentals for 2026

A coastal town with a prominent lighthouse on a hill, surrounded by houses and greenery.

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Our top choices for Winthrop vacation rentals

A hallway with a framed artwork of a person and a colorful bird illustration on the wall.

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

Winthrop

Edmund W.

CA $296 total

includes taxes & fees

Dec 7 - Dec 8

A dining area with a round table set for four, a sofa in the background, and a decorative wall piece.

2. Steps from the ocean - minutes from Boston

Winthrop

CA $546 total

includes taxes & fees

Nov 18 - Nov 19

A modern kitchen with wooden cabinets, a refrigerator, and a dining area with chairs.

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

Winthrop

"We used this apartment as home base for our weekend in Salem and Boston. An easy drive to both, the apartment was easy to get to, and check-in was a breeze. This is not 5-star accommodations, but it was very comfortable and was perfect for our weekend adventures. The host was responsive to my questions and the whole thing went smoothly. We’d recommend the apartment to others looking for an easy, safe place to stay for a trip to the Boston area."

Kristen S.

CA $585 total

includes taxes & fees

Nov 13 - Nov 14

A modern lobby with a wooden panel wall, a beige sofa, a patterned rug, and a large abstract painting.

4. Global Luxury Suites Downtown Boston

Chinatown

Yelitza

CA $332 total

includes taxes & fees

Dec 7 - Dec 8

A row of brick townhouses with fire escapes, a brick sidewalk, and potted plants.

5. Maverick Suites at 40 Temple St

Beacon Hill

Andrea

CA $246 total

includes taxes & fees

Dec 2 - Dec 3

A row of brick buildings with storefronts, including a bakery and a liquor store.

6. Maverick Suites at 245 Newbury St

Back Bay

Chloe

CA $274 total

includes taxes & fees

Dec 6 - Dec 7

A living room with a grey sofa, a black armchair, a coffee table, and a blue rug. There are two windows with blinds, a bookshelf, and a potted plant.

7. Bright 2BR by Boston Waterfront

East Boston

Bridget

CA $467 total

includes taxes & fees

Nov 30 - Dec 1

A bedroom with a bed, a round table with chairs, a TV, and a large mirror.

8. The Concord Hotel

South End

Rupintal

CA $441 total

includes taxes & fees

Nov 22 - Nov 23

A row of multi-story brick buildings with a central entrance, a flag, and parked cars on the street.

9. Maverick Suites at 28 Fenway

Fenway–Kenmore

Judy

CA $306 total

includes taxes & fees

Dec 6 - Dec 7

A wooden hallway with a patterned floor leading to a door.

10. Maverick Suites at 89 Marion

Coolidge Corner

Edna

CA $252 total

includes taxes & fees

Nov 15 - Nov 16

A white table with a vase of white orchids, a white chair, and a view of a cityscape through a window with a black frame.

11. Maverick Suites at 400 Columbus Ave

South End

Lorne

CA $259 total

includes taxes & fees

Nov 15 - Nov 16

A balcony with a city view, featuring a table with wine glasses and a bottle, and a chair.

12. Marriott Vacation Club® at Custom House, Boston

Downtown Boston

Joseph

CA $373 total

includes taxes & fees

Nov 25 - Nov 26

A neatly made bed with a white comforter and a beige throw blanket, a brown leather chair, a small bedside table with a lamp, and a framed picture on the wall.

13. Pet Friendly - Laundry in Bldg - FIDI

Downtown Boston

Kathryn

CA $327 total

includes taxes & fees

Dec 7 - Dec 8

A marina with boats docked, a red brick building, and modern high-rise apartments in the background.

14. Fun houseboat. Walk to Boston attractions WIFI

Boston

Frank M.

CA $682 total

includes taxes & fees

Dec 7 - Dec 8

A modern living room with a black leather sofa, grey armchairs, a coffee table, and a large window offering a city view.

15. Kasa Boston at Fenway

Fenway–Kenmore

antonio

CA $421 total

includes taxes & fees

Nov 30 - Dec 1

A row of brick townhouses with ornate architectural details, large windows, and a central staircase.

16. Stunning Back Bay Studio Apartment

Back Bay

Chloe

CA $275 total

includes taxes & fees

Dec 7 - Dec 8

A modern living room with a blue wall, a large window, a sofa, a coffee table, and a TV.

17. The Chester Hotel

South End

Tracy

CA $414 total

includes taxes & fees

Nov 23 - Nov 24

18. Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep

Charlestown

Marie T.

CA $740 total

includes taxes & fees

Dec 7 - Dec 8

A bedroom with a wooden nightstand, a white bed, and a white wall.

19. Cozy Studio Steps from Boston Common and Theaters

Bay Village

Gary

CA $366 total

includes taxes & fees

Nov 15 - Nov 16

A modern living room with a wooden floor, white furniture, and large windows with blinds.

20. Warr15-1/1 · Comfy 1br, Minutes to Boston Common, 99 Walk score

Bay Village

Nina C.

CA $328 total

includes taxes & fees

Dec 6 - Dec 7

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Top Winthrop Hotel Reviews

A modern lounge area with a central fire feature, seating arrangements, and decorative wall panels.

Holiday Inn Express Boston Logan Airport - Revere by IHG

Revere

10/10 Excellent

Praful

A spacious lobby with a high ceiling, wooden paneling, a large sofa, and a coffee table.

Comfort Inn & Suites Logan International Airport

Revere

10/10 Excellent

Angela

A modern bar area with a long counter, bar stools, and a television screen.

Hampton Inn Boston - Logan Airport

Revere

10/10 Excellent

Yau Hin

A hotel room with a bed, a desk with a lamp, a TV, and a map on the wall.

Château sur Mer Bed & Breakfast

Winthrop

10/10 Excellent

Excellent location costing $30 for cab ride from downtown Intercontinental hotel to B&B. Public transit near by to their subway system. King Bed was comfortable with lots of blankets in a very clean house. They have 4 rooms. Breakfast included yogurt, juices, cereal, fresh fruit, boiled eggs, cheese, ham, sausage, toast and coffee. Joan was very friendly and helpful. Would definitely stay here again.

John

A waterfront patio with outdoor seating, a fire pit, and a city skyline in the background.

Hyatt Regency Boston Harbor

East Boston

10/10 Excellent

Pavel

A beach view with a wooden structure and a concrete walkway.

The Winthrop Arms Hotel And Restaurant

Winthrop

10/10 Excellent

This little gem is only 20 minutes on the train from Boston. When you get there after a long day of touring, you can go and sit on the beach and really appreciate the serenity of the moment. This place has an Old Time Charm. The staff is fantastic. They really make you feel at home. You better be hungry if you eat in the restaurant because the portions are quite substantial. The rooms are a nice size and very clean. We liked it so much, we plan on making the Winthrop Arms our home base next...

Dan

A hotel room with a bed, desk, chair, and a view of the city.

avid hotel Boston Logan Airport - Revere by IHG

Revere

10/10 Excellent

Paul Michael

An outdoor seating area with a fire pit, sofas, and chairs.

Hyatt Place Boston/Seaport District

Seaport District

10/10 Excellent

Brian

A waterfront cityscape with a variety of buildings, including a prominent clock tower and modern skyscrapers.

Battery Wharf Hotel, Boston Waterfront

North End

10/10 Excellent

Miriam

An outdoor cafe with tables and chairs, a building entrance, and a street sign.

Harborside Inn Of Boston

Downtown Boston

10/10 Excellent

Wendy

A modern hotel with a prominent Hampton Inn sign, featuring a multi-story structure with a central courtyard and a landscaped area.

Hampton by Hilton at the Boston Seaport District

Seaport District

10/10 Excellent

Liam

A modern restaurant with round tables and chairs, large windows with a city view, and a geometric patterned floor.

Omni Boston Hotel at the Seaport

Seaport District

10/10 Excellent

Darlene

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, cottages, cabins, villas... 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winthrop vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winthrop vacation rentals we have selected for you start as low as CA $100 per night. Entering your travel dates in the search wizard 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.

Winthrop Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winthrop vacation rentals

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

2. Steps from the ocean - minutes from Boston

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

4. Global Luxury Suites Downtown Boston

5. Maverick Suites at 40 Temple St

6. Maverick Suites at 245 Newbury St

7. Bright 2BR by Boston Waterfront

8. The Concord Hotel

9. Maverick Suites at 28 Fenway

10. Maverick Suites at 89 Marion

11. Maverick Suites at 400 Columbus Ave

12. Marriott Vacation Club® at Custom House, Boston

13. Pet Friendly - Laundry in Bldg - FIDI

14. Fun houseboat. Walk to Boston attractions WIFI

15. Kasa Boston at Fenway

16. Stunning Back Bay Studio Apartment

17. The Chester Hotel

18. Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep

19. Cozy Studio Steps from Boston Common and Theaters

20. Warr15-1/1 · Comfy 1br, Minutes to Boston Common, 99 Walk score

Find vacation rentals that suit your style

Top Winthrop Hotel Reviews

Holiday Inn Express Boston Logan Airport - Revere by IHG

10/10 Excellent

Find out more about Winthrop

Winthrop vacation rentals: An excellent choice for every season

How to find incredible deals on Winthrop rentals