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Massachusetts Rentals with Pools

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158 cabins in Massachusetts with pools

Skip to beach! Condo across from beach!

Dennis Port condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 40 minutes

Match: Swimming pool

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Price per night from

$172

Ocean View Condo across from Beach with pool!

Dennis Port condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 26 minutes

Match: Swimming pool

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Price per night from

$171

Mariner Motor Lodge

West Yarmouth hotel apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 43 minutes

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Price per night from

$136

Big Studio near Longwood Medical area

Brookline apartment

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$114

Peaceful Getaway Cottage on grounds of historic mid-century gem

Northborough house

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$287

Cape Cod Resort with Private Beach

Dennis Port house

1 bedroom / 1 bathroom / sleeps 5

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Price per night from

$268

Cape Cod Retreat with Deck - 2 Miles to Beaches!

Teaticket house

4 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 1 hour 51 minutes

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Price per night from

$202

Oliver's Cottage

West Yarmouth cottage

5 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 1 hour 16 minutes

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Price per night from

$570

Berkshires: Romantic Cottage with spectacular view

Great Barrington cottage

1 bedroom / 1 bathroom / sleeps 3

“Perhaps the most relaxing vacation I've ever had” The Sigels' cottage was absolutely perfect for us. My husband and I were looking for a nice quiet 4-night stay while our 7-yr-old twins visited with their grandparents. When we arrived everything looked just as in the pictures. The room is sunny, but stays nice and cool too (we were there in august). There is an overhead fan but we didn't even need it. The Sigels made us feel very much at home, but they also seemed to know that we were not looking for a chatty B&B; experience. There are plenty of little touches like a bottle of wine waiting for us, tea, sugar, and some other basics in the kitchenette. A hair dryer, eye shade in the bedside table, etc. But nothing seemed overly fussy-- they are naturally good hosts. The pool was absolutely perfect. Big enough to swim laps, but small enough to be a nice temperature. We spent one whole morning just floating in the pool. The view from the pool is stunning. I am sure there are some amazing hikes around (I had broken my tailbone so hiking will have to wait for next year). Great Barrington is a wonderful town too, so if you're wondering where to stay in the Berkshires, then you would be wise to choose GB. It's not huge, but we never really left town. The walkable part of town has great diners, a cool little coffee shop, a movie theatre, used book store, and great music and food at the Gypsy Joynt (a member of the family that owns it-- Jordan Weller-- put out the best CD I've heard in a long time!) On our last night there the Sigels suggested we go to the Guthrie Center for an open mic where we heard more great music. I can't say enough about the Seigel's cottage. We can't wait to go back next summer.

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Price per night from

$273

Eight bedroom home sleeping 20 with private swimming pool

Harwich house

8 bedrooms / 2 bathrooms / sleeps 20

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Price per night from

$714

Six bedroom sleeping 20 with private swimming pool

West Harwich house

6 bedrooms / 2 bathrooms / sleeps 20

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Price per night from

$643

GORGEOUS Home with Pool and Central A/C 106854

Eastham house

5 bedrooms / 3 bathrooms / sleeps 9

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Price per night from

$1,114

LARGE CUSTOM HOME WITH POOL IN WEST FALMOUTH 117899

Falmouth house

6 bedrooms / 7 bathrooms / sleeps 14

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Price per night from

$1,429

Whispering Pines - Cottage 13 126193

Eastham house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$186

61 Chase Ave

Dennis Port apartment

1 bedroom / 1 bathroom / sleeps 4

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Price per night from

$171

1 bedroom condo-just steps to the beach

Dennis Port house

1 bedroom / 2 bathrooms / sleeps 4

“Very cute condo close to beach” I stayed at 194 Captain Chase #8 for a week in August 2015. The condo is very cute and spacious. What I liked best: Location, location location! I love Dennis Port - you are centrally located and it isn't far for a ride up to Provincetown, Chatham, or Hyannis. You are close to the Bay beaches or the National Seashore.There are plenty of restaurants (that you can order out from), pizza places, the Dog House and Sundae School (for ice cream) is right up the road. Glendon Road Beach is a very short walk so making the trek with chairs, a cooler, and a beach bag was not an issue. (and you save yourself a parking fee). The Del Ray Beach Club is very quiet which I liked and after a day at the beach, relaxing by the pool was very nice. The condo was very cute and just like the pictures. The bedroom is very spacious; plenty of room to hang your clothes. Having two bathrooms was wonderful. The living area is also spacious. We had one of the couches made into a bed the entire stay - but still had another couch to sit on to watch TV. The owner has provided some board games, DVD's, and books - even two beach chairs! It was hot the entire week so we made use of the air conditioning. My only issue during the week was trying to cook on the stove. I set off one of the smoke/fire alarms and it took awhile for them to stop beeping. I ended up not using the stove the rest of the week. Overall this rental is ideal spot for a week out at the Cape. I recommend it for a couple, or a couple with young children.

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Price per night from

$100

High-end Brewster ,Mass. Bay view town home

Brewster apartment

2 bedrooms / 2 bathrooms / sleeps 5

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Price per night from

$407

BEAUTIFUL SUNNY HOME IN EDGARTOWN WITH POOL

Edgartown house

5 bedrooms / 4 bathrooms / sleeps 8

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Price per night from

$857

Luxury 8br 7ba Home, Pool,guest House

Nantucket house

8 bedrooms / 8 bathrooms / sleeps 22

“Perfect Home” Our family was lucky enough to stay in this beautiful house from 9/13 - 9/22/13. The house itself is great. The furnishings, finishes, quality and layout are perfect. The best part of the property, in our opinion, is the outdoor living space. We spent a lot of time hanging-out on the rear porch. The rear porch has high-end comfortable furniture, a beautiful fireplace and a meticulously maintained and fenced backyard. The overall setting is ideal and actually, this sounds corny, but the setting seemed like it was from a storybook. Just perfect! I highly recommend this property.

Responds fast! avg. 3 hours 1 minutes

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Price per night from

$2,171

55 Barley Neck Rd 131073

East Orleans house

5 bedrooms / 4 bathrooms / sleeps 10

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Price per night from

$643

Luxury Waterfront Home With Heated Pool

Orleans house

4 bedrooms / 5 bathrooms / sleeps 10

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Price per night from

$1,303

BEAUTIFUL EDGARTOWN COLONIAL WITH POOL

Edgartown house

4 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$1,071

Spectacular luxury Edgartown waterfront home

Edgartown house

6 bedrooms / 5 bathrooms / sleeps 12

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Price per night from

$3,571

Cape Cod cottage-Just 150 feet to Sea Street Beach

Dennis Port house

2 bedrooms / 1 bathroom / sleeps 4

“Classic Cape Cottage” Stayed a week and thoroughly enjoyed it. The outdoor shower was not advertised but a welcome surprise.

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Price per night from

$250

LUXURY WATERFRONT WITH POOL & HIGH END AMENITIES

Edgartown house

6 bedrooms / 6 bathrooms / sleeps 10

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Price per night from

$5,000

Tentrr Signature Site - Great Barrington Campsite - with Goats and Pool!

Great Barrington tented camp

1 bedroom / 1 bathroom / sleeps 4

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Price per night from

$103

Brewster Poolside Retreat

Brewster log cabin

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 hours 17 minutes

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Price per night from

$881

Private Beach Access with Salt Water Pool

Brewster house

5 bedrooms / 5 bathrooms / sleeps 10

Responds fast! avg. 3 hours 17 minutes

Match: Swimming pool

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Price per night from

$1,882

Beautiful Cape with Pool and Air Conditioning Close to Town

Edgartown house

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$429

New Contemporary Home with Heated Pool

Edgartown house

5 bedrooms / 4 bathrooms / sleeps 12

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Price per night from

$1,429

East Falmouth Home: 3-Min Walk to Private Beach!

Waquoit house

5 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 1 hour 51 minutes

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Price per night from

$590

Beautiful Colonial Home in Edgartown with Pool

Edgartown house

4 bedrooms / 4 bathrooms / sleeps 8

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Price per night from

$1,429

Beautiful Katama Home with Heated Pool

Edgartown house

5 bedrooms / 4 bathrooms / sleeps 15

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Price per night from

$714

Bright and airy Edgartown home

Edgartown house

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$279

CLASSIC COLONIAL LUXURY HOME IN EDGARTOWN WITH A HEATED POOL

Edgartown house

5 bedrooms / 5 bathrooms / sleeps 10

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Price per night from

$1,429

Luxury Edgartown Village Home with Pool

Edgartown house

4 bedrooms / 4 bathrooms / sleeps 10

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Price per night from

$857

Beautiful five bedroom home with private swimming pool

Dennis Port house

5 bedrooms / 4 bathrooms / sleeps 10

“Excellent accommodations” The rental agent as well as the owner are easily accessible and ensure the house is ready upon arrival. The owner is gracious and gives a thorough explanation of how to use the pool, jacuzzi and fire pit. Walks to the beach are quite easy from this home.

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Price per night from

$642

2/10 Mile to Nauset Beach

Orleans house

3 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 3 hours 17 minutes

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Price per night from

$1,489

Viewing 38 of 158
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