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919 Houses

8

A private, clean, quiet, room at a house in Winchester.Close to train 93 and 95.

Massachusetts / Winchester

Winchester room

1 1 1 night min

  • 1 bedroom
  • sleeps 1
  • 1 night min
  • Child Friendly
  • Air conditioning

Price per night from

$40

Price per night from

$40

(1) Excellent 

4

Nice room in a quiet New England town

Massachusetts / Winchester

Winchester apartment

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Nearest beach 10 mi
  • Swimming pool
  • Ski

Price per night from

$58

Price per night from

$58

Great rentals within 20 miles that match your search

Distance approx 4.63 km from Winchester

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 7.12 km from Winchester

27

Spacious condo with private balcony, city views, and shared pool access!

Massachusetts / Boston

Boston house

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$193

Price per night from

$193

Distance approx 19.58 km from Winchester

24

Charming Colonial Overlooking Ocean

Massachusetts / Hull

Hull house

3 6 1 night min

  • 3 bedrooms
  • sleeps 6
  • 1 night min
  • Child Friendly

Price per night from

$360

Price per night from

$360

Distance approx 12.99 km from Winchester

6

Boston a la Francaise

Massachusetts / Needham

Needham house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Child Friendly

Price per night from

$344

Price per night from

$344

Distance approx 8.45 km from Winchester

20

Top Floor Apartment

Massachusetts / Newton

Newton apartment

4 8 1 night min

  • 4 bedrooms
  • sleeps 8
  • 1 night min
  • Child Friendly

Price per night from

$217

Responds fast!
avg. 1 hour 10 minutes

Price per night from

$217

Distance approx 8.19 km from Winchester

(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 16.87 km from Winchester

(10) Very Good 

13

THREE SEPARATE BEDROOMS 1700s Fletcher Tavern B&B

Massachusetts / Westford

Westford b and b

3 5 2 nights min

  • 3 bedrooms
  • sleeps 5
  • 2 nights min
  • Nearest beach 5 mi
  • Ask about children
  • Air conditioning
“Wonderful stay in a beautiful home” Just returned from a 3 night stay. The home was beautiful and the owner gracious and kind. Had great conversation at breakfast - which was excellent food. The owner Elizabeth Fletcher went out of her way in all a
…see more

Price per night from

$149

Price per night from

$149

Distance approx 14.27 km from Winchester

18

Executive modern oceanview hilltop home

Massachusetts / Martha's Vineyard

Martha's Vineyard house

4 9 7 nights min

  • 4 bedrooms
  • sleeps 9
  • 7 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$1,031

Price per night from

$1,031

Distance approx 10.62 km from Winchester

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 7.56 km from Winchester

(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 7.26 km from Winchester

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 9.59 km from Winchester

15

Affordable & Convenient Private Room with Airbed!

Massachusetts / Boston

Boston apartment

1 1 30 nights min

  • 1 bedroom
  • sleeps 1
  • 30 nights min
  • Car not necessary

Price per night from

$46

Responds fast!
avg. 3 hours 40 minutes

Price per night from

$46

Distance approx 7.29 km from Winchester

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 10.18 km from Winchester

18

Sunny & Cozy 2 bdrm Duplex, Jamaica Plain, Boston

Massachusetts / Boston

Boston apartment

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$287

Price per night from

$287

Distance approx 5.63 km from Winchester

5

Cambridge Trip Decker

Massachusetts / Cambridge

Cambridge apartment

1 2 1 night min

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

Price per night from

$1,145

Price per night from

$1,145

Distance approx 12.06 km from Winchester

4

Colonial Home

Massachusetts / Dedham

Dedham guest house

1 1 2 nights min

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

Price per night from

$63

Price per night from

$63

Distance approx 3.78 km from Winchester

1

4 BR Medford Square

Massachusetts / Medford

Medford house

4 4 1 night min

  • 4 bedrooms
  • sleeps 4
  • 1 night min

Price per night from

$573

Price per night from

$573

Distance approx 7.58 km from Winchester

24

UltraLuxe Apt in Boston Brownstone in Prime Area 2

Massachusetts / Brookline

Brookline apartment

4 8 3 nights min

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

Price per night from

$1,202

Responds fast!
avg. 2 hours 32 minutes

Price per night from

$1,202

Distance approx 12.01 km from Winchester

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 8.42 km from Winchester

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 3.72 km from Winchester

4

Big Malden Room Minutes to Train (OU1)

Massachusetts / Malden

Malden room

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Air conditioning
  • Pet Friendly

Price per night from

$65

Price per night from

$65

Distance approx 9.58 km from Winchester

14

Beautiful Design, Perfect Location and enough space for a large group

Massachusetts / Boston

Boston condo

4 10 3 nights min

  • 4 bedrooms
  • sleeps 10
  • 3 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$802

Price per night from

$802

Distance approx 7.96 km from Winchester

7

Beautiful Garden Apartment in Coolidge Corner

Massachusetts / Brookline

Brookline apartment

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Child Friendly

Price per night from

$109

Price per night from

$109

Distance approx 8.61 km from Winchester

(2)  

9

Boston Harbor View 1 Bedroom Luxury Suites

Massachusetts / Boston

Boston apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Pet Friendly

Price per night from

$143

Price per night from

$143

Distance approx 7.31 km from Winchester

14

Luxury Top Floor 2 Bedroom in the Heart of Boston's North End

Massachusetts / Boston

Boston apartment

2 4 30 nights min

  • 2 bedrooms
  • sleeps 4
  • 30 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$201

Price per night from

$201

Distance approx 5.97 km from Winchester

4

Convenient 2 bed apartment for short term letting.... ideal for Harvard/MIT

Massachusetts / Cambridge

Cambridge apartment

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Air conditioning

Price per night from

$138

Price per night from

$138

Distance approx 4.63 km from Winchester

4

Beautiful Spacious Room (S1-3)

Massachusetts / Somerville

Somerville room

1 1 1 night min

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

Price per night from

$64

Price per night from

$64

Distance approx 7.67 km from Winchester

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 6.42 km from Winchester

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 13.69 km from Winchester

22

Serene space in Milton

Massachusetts / Milton

Milton apartment

3 6 2 nights min

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

Price per night from

$229

Price per night from

$229

Distance approx 6.83 km from Winchester

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 10.19 km from Winchester

(1) Average 

17

Georgia Hill Garden Suite 1

Massachusetts / Boston

Boston apartment

3 12 5 nights min

  • 3 bedrooms
  • sleeps 12
  • 5 nights min
  • Nearest beach 2 mi
  • Child Friendly
  • Air conditioning

Price per night from

$515

Price per night from

$515

Distance approx 8.61 km from Winchester

(4)  

10

Boston Harbor View Luxury Suites

Massachusetts / Boston

Boston house

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$143

Price per night from

$143

Distance approx 8.29 km from Winchester

(1)  

10

Global Luxury Suites in South End

Massachusetts / Boston

Boston apartment

3 5 min stay varies

  • 3 bedrooms
  • sleeps 5
  • min stay varies
  • Child Friendly
  • Pet Friendly

Price per night from

$194

Responds fast!
avg. 35 minutes

Price per night from

$194

Distance approx 7.46 km from Winchester

(22) Excellent 

29

Boston North End luxury apartment.

Massachusetts / Boston

Boston apartment

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Ask about children
  • Car not necessary
  • Air conditioning
“Perfect North End Rental” We loved this super clean one bedroom in the heart of the North End of Boston. Furniture, decor and amenities made us feel right at home. Bonus: we were within walking distance of everything wonderful about Boston i.e. highl
…see more

Price per night from

$220

Price per night from

$220

Distance approx 7.67 km from Winchester

4

TEST PROPERTY - FLIPKEY

Georgia / Boston

Boston house

4 1 1 night min

  • 4 bedrooms
  • sleeps 1
  • 1 night min

Price per night from

$11,447

Price per night from

$11,447