Winthrop Rentals

Close

Enter dates for more accurate prices

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more

934 Houses

4

Queen One Bedroom Suite

Massachusetts / Winthrop

Winthrop hotel apartment

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Child Friendly

Price per night from

$297

Price per night from

$297

4

King Studio

Massachusetts / Winthrop

Winthrop hotel apartment

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$217

Price per night from

$217

Great rentals within 20 miles that match your search

Distance approx 5.54 km from Winthrop Show on Map

5

Beautiful Spacious Room (SU2-2)

Massachusetts / Somerville

Somerville room

1 1 1 night min

  • 1 bedroom
  • sleeps 1
  • 1 night min
  • Air conditioning
  • Private garden

Price per night from

$69

Price per night from

$69

Distance approx 7.45 km from Winthrop Show on Map

(17) Very Good 

24

Arthouse - Boston Brewery District Condo

Massachusetts / Boston

Boston apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly
“Great place for a family visit to Boston” We stayed at the Arthouse for 2 days in August. It's extremely handy for the T (underground) into town, on a quiet street. The neighbourhood looked nice too, wish we had had more time to look around. We parked
…see more

Price per night from

$284

Responds fast!
avg. 2 hours 24 minutes

Price per night from

$284

Distance approx 4.26 km from Winthrop Show on Map

(53) Excellent 

Certificate of Excellence

14

Beacon Hill -- "the Nest" sunny studio

Massachusetts / Boston

Boston condo

1 2 28 nights min

  • 1 bedroom
  • sleeps 2
  • 28 nights min
  • Car not necessary
  • Air conditioning
“The Nest” A very nice and charming apartment in Beacon Hill. We were looking for a vacation place that would give us the feeling of living in Boston, rather than a "we-could-be-anywhere" hotel room. The owner has gone to great lengths to make the stud
…see more

Certificate of Excellence

Price per night from

$274

Responds fast!
avg. 3 hours 24 minutes

Price per night from

$274

Distance approx 17.83 km from Winthrop

16

Second Floor: 2+ Bedroom, 1.25 Bath

Cape Ann / Manchester-by-the-Sea

Manchester-by-the-Sea condo

3 5 4 nights min

  • 3 bedrooms
  • sleeps 5
  • 4 nights min
  • Child Friendly

Price per night from

$287

Price per night from

$287

Distance approx 2.44 km from Winthrop Show on Map

(22) Excellent 

Certificate of Excellence

30

New lux. Apt.private roof deck harbor/skyline

Massachusetts / Boston

Boston apartment

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Child Friendly
  • Car not necessary
  • Air conditioning

Certificate of Excellence

Price per night from

$401

Responds fast!
avg. 1 hour 38 minutes

Price per night from

$401

Distance approx 3.97 km from Winthrop Show on Map

16

Fully Furnished-Best View!!

Massachusetts / Nahant

Nahant house

2 3 5 nights min

  • 2 bedrooms
  • sleeps 3
  • 5 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$367

Responds fast!
avg. 1 hour 39 minutes

Price per night from

$367

Distance approx 3.31 km from Winthrop Show on Map

(7) Very Good 

16

Houseboat in Boston Harbor

Massachusetts / Boston

Boston houseboat

1 6 min stay varies

  • 1 bedroom
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$201

Responds fast!
avg. 2 hours 41 minutes

Price per night from

$201

Distance approx 3.46 km from Winthrop Show on Map

(53) Excellent 

23

The Golden Slipper, B&B Afloat and Charter

Massachusetts / Boston

Boston yacht

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Air conditioning
“The best way to enjoy Boston” Staying at the Golden Slipper Bed & Breakfast afloat was like having two vacations at the same time for the price of one. Not only you get to enjoy all what historic Boston has to offer --- the actual places where the nat
…see more

Price per night from

$314

Price per night from

$314

Distance approx 10.37 km from Winthrop

(1)  

18

Batcave

Massachusetts / Milton

Milton house

3 6 5 nights min

  • 3 bedrooms
  • sleeps 6
  • 5 nights min
  • Nearest beach 5 mi
  • Child Friendly
  • Air conditioning

Price per night from

$148

Price per night from

$148

Distance approx 3.86 km from Winthrop Show on Map

10

Beautiful, new, one bedroom, amazing location

Massachusetts / Boston

Boston apartment

1 3 3 nights min

  • 1 bedroom
  • sleeps 3
  • 3 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$201

Price per night from

$201

Distance approx 6.71 km from Winthrop Show on Map

20

Ocean Front Retreat Close to Boston

Massachusetts / Lynn

Lynn house

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min

Price per night from

$223

Price per night from

$223

Distance approx 1.87 km from Winthrop Show on Map

9

1 minute to T and beach, 15mins to downtown Boston

Massachusetts / Revere

Revere apartment

4 7 1 night min

  • 4 bedrooms
  • sleeps 7
  • 1 night min
  • Suitable for children age 5+
  • Car not necessary
  • Air conditioning

Price per night from

$399

Responds fast!
avg. 3 hours 24 minutes

Price per night from

$399

Distance approx 7 km from Winthrop Show on Map

6

BU+Longwood+MIT bus 1bdrm+sofa bed

Massachusetts / Brookline

Brookline apartment

1 4 4 nights min

  • 1 bedroom
  • sleeps 4
  • 4 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$257

Price per night from

$257

Distance approx 4.42 km from Winthrop Show on Map

8

Cozy Beacon Hill One Bedroom Apartment

Massachusetts / Boston

Boston apartment

1 2 4 nights min

  • 1 bedroom
  • sleeps 2
  • 4 nights min
  • Child Friendly

Price per night from

$229

Price per night from

$229

Distance approx 8.87 km from Winthrop

8

Wonderful, Sunny and Big Bedroom beautiful house

Massachusetts / Boston

Boston house

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$229

Responds fast!
avg. 9 minutes

Price per night from

$229

Distance approx 7.29 km from Winthrop Show on Map

20

Luxury Brand New 3br / 2ba Boston Brookline Exceptional Location!!

Massachusetts / Brookline

Brookline apartment

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$429

Responds fast!
avg. 1 hour 17 minutes

Price per night from

$429

Distance approx 7.78 km from Winthrop Show on Map

(3) Very Good 

57

Architectural, Accessible, Charming House

Massachusetts / Boston

Boston house

4 7 6 nights min

  • 4 bedrooms
  • sleeps 7
  • 6 nights min
  • Child Friendly
  • Air conditioning
  • Ask about pets
“Sisters Get Away Vacation” This house is perfect for someone with a disability that requires them to stay in a wheelchair. When I started looking for a house near Boston that had accessibility, I found it to be a daunting task. Then I found this hou
…see more

Price per night from

$630

Price per night from

$630

Distance approx 6.24 km from Winthrop Show on Map

(2) Excellent 

7

3br/1140sf Cambridge Winter Rental By Harvard Sq.

Massachusetts / Cambridge

Cambridge apartment

3 4 30 nights min

  • 3 bedrooms
  • sleeps 4
  • 30 nights min
  • Child Friendly
  • Ask about pets

Price per night from

$107

Price per night from

$107

Distance approx 8.19 km from Winthrop

(2) Very Good 

46

Harvard/MIT/Mass General/Boston Univ/ Cambridge

Massachusetts / Cambridge

Cambridge apartment

4 12 min stay varies

  • 4 bedrooms
  • sleeps 12
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 48 mi
  • Child Friendly

Price per night from

$355

Price per night from

$355

Distance approx 7.38 km from Winthrop Show on Map

7

Luxury 2 Bedroom 2 Bath Apartment Fenway Park Boston

Massachusetts / Brookline

Brookline apartment

2 5 1 night min

  • 2 bedrooms
  • sleeps 5
  • 1 night min
  • Nearest beach 10 mi
  • Child Friendly
  • Car not necessary

Price per night from

$513

Price per night from

$513

Distance approx 4.11 km from Winthrop Show on Map

22

Off Broadway in South Boston

Massachusetts / Boston

Boston house

5 8 4 nights min

  • 5 bedrooms
  • sleeps 8
  • 4 nights min
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$803

Price per night from

$803

Distance approx 8.04 km from Winthrop Show on Map

6

A beautifully renovated apartment in the trees

Massachusetts / Boston

Boston apartment

3 4 3 nights min

  • 3 bedrooms
  • sleeps 4
  • 3 nights min
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$344

Responds fast!
avg. 1 hour 43 minutes

Price per night from

$344

Distance approx 4.61 km from Winthrop Show on Map

4

One bedroom in historic Beacon Hill brownstone just steps away from the Common!

Massachusetts / Boston

Boston apartment

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Child Friendly

Price per night from

$229

Price per night from

$229

Distance approx 7.88 km from Winthrop Show on Map

11

Beautiful Newly Built 2BR Minutes to City Center

Massachusetts / Brookline

Brookline apartment

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$113

Price per night from

$113

Distance approx 3.4 km from Winthrop Show on Map

6

Nice room in Charlestown

Massachusetts / Boston

Boston condo

1 2 7 nights min

  • 1 bedroom
  • sleeps 2
  • 7 nights min

Price per night from

$80

Price per night from

$80

Distance approx 4.31 km from Winthrop Show on Map

8

Stunning west end beauty walk to MGH and cambridg

Massachusetts / Boston

Boston apartment

1 2 30 nights min

  • 1 bedroom
  • sleeps 2
  • 30 nights min
  • Air conditioning

Price per night from

$134

Price per night from

$134

Distance approx 7.66 km from Winthrop Show on Map

8

Beautiful 2.5 bedroom minutes from Boston

Massachusetts / Brookline

Brookline apartment

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$183

Price per night from

$183

Distance approx 11.04 km from Winthrop

5

Cozy Room in Renovated Apartment

Massachusetts / Watertown

Watertown apartment

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Private garden

Price per night from

$23

Price per night from

$23

Distance approx 9.43 km from Winthrop

29

Sunny 2 Bedrooms Victorian Fully Furnished Condo

Massachusetts / Boston

Boston apartment

2 2 30 nights min

  • 2 bedrooms
  • sleeps 2
  • 30 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$83

Responds fast!
avg. 2 hours 47 minutes

Price per night from

$83

Distance approx 4.02 km from Winthrop Show on Map

15

G2 Luxury Queen Anne Style Townhouse 3 Bedrooms 2 baths with parkings

Massachusetts / Boston

Boston apartment

1 10 5 nights min

  • 1 bedroom
  • sleeps 10
  • 5 nights min
  • Nearest beach 2 mi
  • Child Friendly
  • Car not necessary

Price per night from

$400

Price per night from

$400

Distance approx 3.29 km from Winthrop Show on Map

23

Boston Harbor Yacht

Massachusetts / Boston

Boston yacht

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$399

Responds fast!
avg. 2 hours 41 minutes

Price per night from

$399

Distance approx 7.58 km from Winthrop Show on Map

8

BEAUTIFUL AND SPACIOUS 3BR 3BATH WITH PRIVATE DECK

Massachusetts / Brookline

Brookline apartment

3 7 3 nights min

  • 3 bedrooms
  • sleeps 7
  • 3 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$571

Price per night from

$571

Distance approx 4.43 km from Winthrop Show on Map

4

Renovated Studio Apartment

Massachusetts / Boston

Boston apartment

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Air conditioning

Price per night from

$229

Price per night from

$229

Distance approx 4.02 km from Winthrop Show on Map

32

T4 Brownstone Style right in the City of Boston

Massachusetts / Boston

Boston apartment

1 2 5 nights min

  • 1 bedroom
  • sleeps 2
  • 5 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$401

Price per night from

$401

Distance approx 5.5 km from Winthrop Show on Map

24

Back Bay 2 Bedroom Apartments near Fenway Park

Massachusetts / Boston

Boston apartment

2 6 5 nights min

  • 2 bedrooms
  • sleeps 6
  • 5 nights min
  • Child Friendly

Price per night from

$686

Responds fast!
avg. 2 hours 15 minutes

Price per night from

$686

Distance approx 4.21 km from Winthrop Show on Map

15

Colbyco D Street - South Boston, MA

Massachusetts / Boston

Boston condo

3 8 3 nights min

  • 3 bedrooms
  • sleeps 8
  • 3 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$571

Price per night from

$571