50 Best Massachusetts Apartments on Holiday Lettings - Vacation rentals

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3,085 properties
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Ipswich
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Waltham
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Newbury
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Brookline
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Hampshire County
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South Chelmsford
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Marlborough
7 properties

Massachusetts

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5,203 Vacation rentals

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(6) Very Good 

24

Vacation cottage with golf nearby in New Seabury

Cape Cod / New Seabury

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Child friendly
Lovely open-plan home furnished in comfortable, casual style. Fully-equipped kitchen with counter seating, dining area and sitting area with TV, flow into second step-down sitting area which opens with sliding glass doors onto deck and back yard. Master bedroom (with  …see more

from $145 / night

$995 - $2695 / week

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from $145 / night

(19) Excellent 

65

Apartment rental in Boston

Massachusetts / Boston

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
Contemporary One Bedroom, One Bath fully furnished condominium home (711 SF) at a Luxury Condominiums Building at the Boston/Charlestown historic Navy Yard, on the waterfront of Boston Harbor, situated right on the freedom trail and historic attractions such as the USS  …see more

from $149 / night

$851 - $1595 / week

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from $149 / night

4

Home rental in Massachusetts

Massachusetts / Lowell

3 4 1 night min

  • 3 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning
  • Private garden
Our house is 5 minutes walk from restaurants,coffee shops, laundry, salon, and UMass Lowell. DOWNSTAIRS Bathroom - Sink and toilet, shampoo, soap. Dining area: Table and 4 chairs. Kitchen - New refrigerator, Gas stove, microwave, dishwasher, toaster. pots, pans, cups,  …see more

from $100 / night

$700 / week

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from $100 / night

(3) Excellent 

24

Vacation apartment rental

Massachusetts / Plymouth

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Child friendly
A beautiful one-bedroom with additional queen sleep-sofa in the heart of historic Plymouth harbor is waiting for you. Not more than 15 yards to the water and a 3-minute walk to the Mayflower and Plymouth Rock, this location couldn't be better for a vacation rental  …see more

from $235 / night

$1300 / week

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from $235 / night

(3) Excellent 

44

Vacation home in South Chatham

Chatham / South Chatham

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 0.6 mi
  • Child friendly
  • Air conditioning
Completely renovated, this year round quaint Cape Cod open concept 1500 sq ft home has 3 bedrooms, 2 baths with a large two level outdoor deck overlooking beautifully landscaped yard. Sleeps 6-8 comfortably. Up to 10 including a pullout sleeper sofa. All rooms are brig  …see more

from $275 / night

$1601 - $4495 / week

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from $275 / night

52

Vacation home in Centerville

Cape Cod / Centerville

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
Close your eyes and imagine the perfect beach house .Well that's what Mc's Shack Beach House . Situated down a leafy lane right on the beach, on your own private stretch of beach. Mc's Shack Beach House is approx 1700 sq ft ,it has 2 large bedrooms ,a  …see more

from $284 / night

$1989 - $2788 / week

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from $284 / night

18

Vacation apartment with shared pool in Massachusetts

Massachusetts / Boston

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This beautiful, spacious apartment is equipped with superior features including European-style cabinetry, floor-to-ceiling windows and environmentally sustainable bamboo flooring. Guests will enjoy the great on-site amenities such as the salt water pool with rooftop dec  …see more

from $149 / night

$1043 / week

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from $149 / night

(10) Very Good 

19

Vacation home in Eastham

Cape Cod / Eastham

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Cosy, welcoming home in South Eastham on the outer Cape. The property is well equipped and with lots of space for families or groups. Our traditional Cape Cod house features 4 bedrooms, 2 baths, a generous open plan living/dining/kitchen leading out to a deck. The hous  …see more

from $204 / night

$1429 / week

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from $204 / night

14

Massachusetts Vacation apartment rental

Massachusetts / Boston

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning
This exquisite, luxury apartment community in Back Bay features landscaped gardens, a private courtyard with elegant cast iron fountains, a roof top terrace with spectacular Boston skyline views and a children's playground. These apartments are located at the cross  …see more

from $169 / night

$1183 / week

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from $169 / night

18

Apartment rental in Massachusetts with shared pool

Massachusetts / Boston

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
1 Bed, 1 Bath, Sleeps 3 Situated right in the heart of Boston, overlooking the beautiful skyline, the builsing’s newly constructed, fully furnished, luxury apartments are beyond compare. Whether you are looking for a relaxing swim in the 25-yard indoor infinity p  …see more

from $180 / night

$1254 / week

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from $180 / night

18

Vacation apartment in Massachusetts

Massachusetts / Boston

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
This apartment is complete with a fully equipped kitchen with stainless steel appliances, a living area, and a spacious bedroom. The community offers spectacular on-site amenities like a lounge area with a fireplace and plasma TV, billiards lounge, exercise classes, sho  …see more

from $129 / night

$903 / week

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from $129 / night

20

Apartment rental in Boston

Massachusetts / Boston

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
This beautiful apartment is complete with a fully equipped designer kitchen with hardwood cabinetry, living area, and a spacious bedroom. Enjoy landscaped gardens, a private courtyard with elegant fountains, a roof top terrace with Boston skyline views, concierge servi  …see more

from $140 / night

$974 / week

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from $140 / night

12

Vacation apartment with shared pool in Massachusetts

Massachusetts / Boston

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This beautifully furnished apartment is complete with a fully equipped kitchen, living area, and a spacious bedroom. The apartment features granite countertops, high ceilings and hardwood floors. Guests can enjoy the indoor heated pool, gaming and internet lounge, cardi  …see more

from $140 / night

$974 / week

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from $140 / night

23

Vacation apartment in Boston

Massachusetts / Boston

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
2 Bed, 2 Bath, Sleeps 5 These newly constructed, luxury apartments epitomize what it means to live well in one of Boston’s most eclectic and vibrant communities. An established neighborhood standout, the building’s apartments offer floor to ceiling windows  …see more

from $215 / night

$1499 / week

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from $215 / night

19

Apartment rental in Massachusetts

Massachusetts / Boston

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
2 Bed, 2 Bath, Sleeps 5 Beginning with the most prestigious of locations and culminating in distinction of style, this building immerses you in the city’s best restaurants and bars, galleries and museums, and culture-focused festivals. Situated in the heart of Pe  …see more

from $180 / night

$1254 / week

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from $180 / night

11

Home rental in Orleans

Cape Cod / Orleans

4 6 3 nights min

  • 4 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
Our home is located in a quiet upscale neighbourhood close to all amenities. Walk to grocery store, downtown shopping, library, tennis courts and town field. Less than a 5 minute drive to ocean and bay. Quick access to highway and all the surrounding Cape towns. Rel  …see more

from $251 / night

$1801 / week

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from $251 / night

20

Vacation apartment with shared pool in Massachusetts

Massachusetts / Boston

2 5 30 nights min

  • 2 bedrooms
  • Sleeps 5
  • 30 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
2 Bed, 2 Bath, Sleeps 5 Formerly known as the Gaiety Theater, The building is located on the site of what was once “Bostons Most Modern Playhouse” dating back to 1908. This newly constructed, eco-friendly 27 floor high-rise is surrounded by beautifully pres  …see more

from $180 / night

$1254 / week

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from $180 / night

16

Vacation apartment with shared pool in Massachusetts

Massachusetts / Boston

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
1 Bed, 1 Bath, Sleeps 3 Situated right in the heart of Boston, overlooking the beautiful skyline, the builsing’s newly constructed, fully furnished, luxury apartments are beyond compare. Whether you are looking for a relaxing swim in the 25-yard indoor infinity p  …see more

from $140 / night

$974 / week

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from $140 / night

27

Massachusetts Vacation apartment accommodation

Massachusetts / Boston

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Child friendly
  • Ask about pets
At this building, guests can enjoy magnificent apartment homes with high ceilings, oversized windows, gourmet kitchens with granite countertops and much more. This luxurious on-site amenities include an outdoor pool, basketball & tennis courts, a movie theater, chil  …see more

from $120 / night

$834 / week

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from $120 / night

19

Vacation apartment in Boston

Massachusetts / Boston

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
2 Bed, 2 Bath, Sleeps 5 Situated right in the heart of Boston, overlooking the beautiful skyline, the builsing’s newly constructed, fully furnished, luxury apartments are beyond compare. Whether you are looking for a relaxing swim in the 25-yard indoor infinity p  …see more

from $249 / night

$1743 / week

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from $249 / night

21

Vacation apartment in Massachusetts

Massachusetts / Boston

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
2 Bed, 2 Bath, Sleeps 5 The building’s historic 19th century façade, its 21st century amenities, intimate courtyard, and landscaped gardens, is truly a home away from home for the most refined traveler. At the crossroads of two of Boston’s most histo  …see more

from $180 / night

$1254 / week

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from $180 / night

23

Vacation apartment in Massachusetts

Massachusetts / Cambridge

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This luxurious apartment features nine-foot ceilings, a spacious living area, bedroom, oversized closet, and fully-equipped kitchen. Amenities include a heated indoor swimming pool, a 2,200 square foot fitness center, a resident lounge with bar, media room, tot room and  …see more

from $129 / night

$903 / week

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from $129 / night

39

Vacation home with golf nearby in West Chatham

Chatham / West Chatham

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Suitable for children age 5+
ACCOMMODATIONS: 3 bedrooms plus den with 2.5 baths. Accommodating 8-10 people. Master suite: king bed w/en suite Guest room 1: queen bed Guest room 2: four twin beds (2 bunks) Guest room 3: den w/full bed Living room Dining room seats 8 (addition kitchen table sea  …see more

from $415 / night

$2201 / week

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from $415 / night

(11) Excellent 

24

Vacation windmill rental

Cape Cod / Centerville

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool
Fernbrook Windmill comprises a modern fully-serviced house built in a Classic Cape style around the original windmill that served the Fernbrook Estate. The original windmill was built in 1881 to draw fresh water for the Fernbrook Estate. A 'Cape Style' additio  …see more

from $1187 / night

$8308 / week

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from $1187 / night

(1) Excellent 

21

Boston Vacation apartment rental

Massachusetts / Boston

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Ask about pets
This furnished apartment is complete with a fully equipped kitchen, living area, and two spacious bedrooms. The apartment features hardwood flooring, expansive windows and stainless steel appliances. Guests can enjoy on-site amenities including a rooftop lounge with gri  …see more

from $180 / night

$1254 / week

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from $180 / night

22

Apartment rental in Massachusetts

Massachusetts / Cambridge

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
2 Bed, 2 Bath, Sleeps 5 This building is located in the heart of Kendall Square in Cambridge, an award winning neighborhood marked as the global center for innovation and technology. Just steps from MIT and dubbed as one of the most exciting places to live, work, shop,  …see more

from $200 / night

$1394 / week

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from $200 / night

20

Massachusetts Vacation apartment rental

Massachusetts / Boston

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This beautiful, spacious apartment is equipped with superior features including European-style cabinetry, floor-to-ceiling windows and environmentally sustainable bamboo flooring. Guests will enjoy the great on-site amenities such as the salt water pool with rooftop dec  …see more

from $209 / night

$1463 / week

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from $209 / night

18

Apartment rental in Massachusetts with shared pool

Massachusetts / Boston

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This beautiful furnished apartment provides you with an entirely equipped kitchen and expansive floorplans. Residing here residents can take advantage of copious delightful amenities such as an outdoor pool, 24-hour concierge, fitness center and many other. This loca  …see more

from $120 / night

$834 / week

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from $120 / night

19

Vacation apartment in Massachusetts

Massachusetts / Boston

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
This beautiful apartment is complete with a fully equipped designer kitchen with hardwood cabinetry, living area, two spacious bedrooms and two bathrooms. Enjoy landscaped gardens, a private courtyard with elegant fountains, a roof top terrace with Boston skyline views  …see more

from $180 / night

$1254 / week

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from $180 / night

(2) Excellent 

19

Apartment rental in Massachusetts

Massachusetts / Boston

1 3 30 nights min

  • 1 bedroom
  • Sleeps 3
  • 30 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
This furnished apartment is complete with a fully equipped kitchen, living area, and a spacious bedroom. The apartment features hardwood flooring, expansive windows and stainless steel appliances. Guests can enjoy on-site amenities including a rooftop lounge with grilli  …see more

from $120 / night

$834 / week

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from $120 / night

21

Vacation apartment in Massachusetts

Massachusetts / Boston

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
2 Bed, 2 Bath, Sleeps 5 The building’s historic 19th century façade, its 21st century amenities, intimate courtyard, and landscaped gardens, is truly a home away from home for the most refined traveler. At the crossroads of two of Boston’s most histo  …see more

from $191 / night

$1331 / week

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from $191 / night

14

Provincetown Vacation condo rental

Cape Cod / Provincetown

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Air conditioning
  • Private garden
A rare historic gem located in Provincetown's Gallery District at the top of Pearl St. This exclusive unit is one of two redeveloped from a 19th-century barn that later served as the Cape School of Art and the studio and residence of the American painter Edwin Dick  …see more

from $486 / night

$3400 / week

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from $486 / night

13

Vacation guest house in Vineyard Haven

Martha's Vineyard / Vineyard Haven

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Suitable for children age 5+
  • Air conditioning
  • Private garden
This property is in downtown Vineyard Haven within the historic district. The barn has a sleeping loft, open living, dining & kitchen area. The efficiency kitchen has a two burner cooktop,under counter refrigerator,coffee maker,microwave and large capacity convec  …see more

from $246 / night

$1716 / week

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from $246 / night

(1) Very Good 

19

Vacation apartment in Boston

Massachusetts / Boston

2 5 30 nights min

  • 2 bedrooms
  • Sleeps 5
  • 30 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
These elegant apartment homes offer high capacity washer/dryer, oak flooring, walk-in closet, GE stainless steel appliances & much more. Residents can enjoy incredible amenities including outdoor swimming pool and fitness center.This luxury green building wa  …see more

from $169 / night

$1183 / week

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from $169 / night

4

Apartment rental in Massachusetts

Massachusetts / Cambridge

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
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from $11 / night

$71 / week

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from $11 / night

22

Vacation apartment in Massachusetts

Massachusetts / Boston

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
1 Bed, 1 Bath, Sleeps 3 These newly constructed, luxury apartments epitomize what it means to live well in one of Boston’s most eclectic and vibrant communities. An established neighborhood standout, the building’s apartments offer floor to ceiling windows  …see more

from $129 / night

$903 / week

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from $129 / night

18

Apartment rental in Massachusetts

Massachusetts / Boston

1 3 30 nights min

  • 1 bedroom
  • Sleeps 3
  • 30 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
1 Bed, 1 Bath, Sleeps 3 A distinctive presence in the Boston skyline, the building’s precise and modern architectural silhouette is inspired by its location at the nexus of several of the city’s most compelling neighborhoods. Overlooking the Rose Kennedy Gr  …see more

from $169 / night

$1183 / week

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from $169 / night

20

Apartment rental in Massachusetts

Massachusetts / Boston

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Ask about pets
1 Bed, 1 Bath, Sleeps 3 These newly constructed, luxury apartments epitomize what it means to live well in one of Boston’s most eclectic and vibrant communities. An established neighborhood standout, the building’s apartments offer floor to ceiling windows  …see more

from $129 / night

$903 / week

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from $129 / night

16

Boston Vacation studio rental

Massachusetts / Boston

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Ask about pets
This beautiful furnished apartment features a fully-equipped, chef-style kitchen with GE stainless steel appliances, a bedroom, walk-in closet, spacious living area and much more. Guests can enjoy on-site amenities including a fitness center with Yoga studio, dog bathin  …see more

from $129 / night

$903 / week

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from $129 / night

6

Vacation home in Massachusetts

Massachusetts / Boston

3 4 Min stay varies

  • 3 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
Quiet but just a minute off the interstate, a great place to stay for a few days. Easy access to Newton, Cambridge or Boston. Lovely deck and backyard to relax in the summer. 3 bedrooms and a playroom spread over 3 floors, a garage. A BBQ and a backyard make your stay v  …see more

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