Guesthouses Massachusetts

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1,038 guest houses

Waterfront Loft in Massapequa, Minutes From the Beach

Massapequa guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Rental types Waterfront

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Price per night from

$149

Nattuary, a Nordic Spa Retreat on the Bay of Fundy

Gardner Creek guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Rental types Waterfront

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Price per night from

$209

The Overlook

Hammond guest house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Rental types Waterfront

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Price per night from

$399

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Oceanside 3

East Sandwich cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Quintessential Cape Cod beach house - yes, the one in your dream” I stayed at this adorable beach house in august of 2011, my first time to beautiful Cape Cod. I could not have imagined it more perfectly; this little cottage is nestled right in the sand, bare foot steps on the beach. Its the perfect size for a couples retreat or a small family. You will feel worlds away from reality in this cozy and comfortable cottage. We enjoyed a fire on the beach, a stroll into East Sandwich for breakfast, many hours lounging in the sun and playing in the sand-bottomed surf. I still dream of this house, and it will always hold a special place in my traveling memories, for it was far too perfect for words. Thank you Jay and Gretchen for sharing your slice of heaven!

1 of 2 match: Rental types, Waterfront

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Price per night from

$114

Romantic Waterfront Artist Cottage

Truro cottage

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

1 of 2 match: Rental types, Waterfront

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Price per night from

$376

Test Property S2-Signup

Birch Harbor boathouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Rental types, Waterfront

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Price per night from

$1,027

SUMMER COTTAGE BY THE SEA

Swans Island house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Waterfront

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Price per night from

$286

Wake up to a stunning view of Narragansett Bay, bridge, & lighthouse

Portsmouth house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Rental types, Waterfront

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Price per night from

$441

Chadwick House

Friendship house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Rental types, Waterfront

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Price per night from

$457

1 of 2 match: Rental types, Waterfront

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Price per night from

$652

C’est La Vue

Siasconset house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Waterfront

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Price per night from

$1,631

Sun Drenched Penthouse with Million Dollar Views

Weehawken apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 50 minutes

1 of 2 match: Rental types, Waterfront

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Price per night from

$345

Waterfront Beach Home With Attached In- Law Suite

Weymouth house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Rental types, Waterfront

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Price per night from

$856

Experience Your Jorney with Us

Mexico house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Rental types, Waterfront

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Price per night from

$213

Oceanfront mini home, two decks, with spectacular views.

Meteghan cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Rental types, Waterfront

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Price per night from

$125

173C North Shore Blvd

East Sandwich cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

“Great cottage! Clean, updated, cair, laundry, outside shower. Hi” This is a wonderful a very comfortable cottage. Great for a family of up to 5. Very modern, hardwood floors, central air, laundry, storage space for bikes, fishing equipment, etc. Quick walk to a very quiet beach. The low tides are awesome! Surrounding cottages are very nice. The town of East Sandwich is very quiet. Great restaurants, ice cream, antiques, etc.

1 of 2 match: Rental types, Waterfront

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Price per night from

$210

95 A Salt Marsh Rd

East Sandwich cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Best Vacation ever!” I love that cabin! My husband and children had the best week! This was our third year at this cabin and we can't wait till nest year. We just loved it!

1 of 2 match: Rental types, Waterfront

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Price per night from

$278

343 Phillips Rd

Sagamore Beach cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

“Beautiful ocean front cottage” Just a small walk to a private beach. You do not have to sit in hours of traffic to go over the bridge to enjoy being at the cape.

1 of 2 match: Rental types, Waterfront

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Price per night from

$269

5 Captain Crocker

East Sandwich cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 7

1 of 2 match: Rental types, Waterfront

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Price per night from

$854

105 North Shore Blvd - B

East Sandwich house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Waterfront

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Price per night from

$319

Smith Heights Vintage Waterfront Cottages- McKechnie

Eastham cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Rental types, Waterfront

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Price per night from

$327

11 Freeman Ave

Sandwich cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Rental types, Waterfront

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Price per night from

$399

Smith Heights Vintage Waterfront Cottages- Gooch

Eastham cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Rental types, Waterfront

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Price per night from

$327

233 Phillips Rd

Sagamore Beach cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Rental types, Waterfront

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Price per night from

$249

36 Salt Marsh Rd.

East Sandwich cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Rental types, Waterfront

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Price per night from

$249

111 North Shore Blvd

East Sandwich cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Rental types, Waterfront

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Price per night from

$240

179 B North Shore Blvd

East Sandwich cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Waterfront

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Price per night from

$214

1 White Cap Path

Sandwich apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Waterfront

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Price per night from

$342

3 White Cap Path

Sandwich apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

“Comfort, breezes, superb views” For older renters this is an ideal setting for walks, long views, easy access to the Canal, route 6a and Sandwich tourist offerings. There's nothing between you and the water - no traffic to negotiate, no noise, no crowds. Do you need a big-screen TV? You've got it.Lots of lounging space? Ditto. Nearness to a market? No problem. A fully-equipped kitchen? It's yours. This is a hidden jewel!

1 of 2 match: Rental types, Waterfront

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Price per night from

$285

95 Salt Marsh Rd

Sandwich cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

“always wonderful” i always have a good time there, i have been going every august for over 10 yrs...cant beat that beach...private quiet...we are often the only people on the beach!!! as far as the cottage, im recommending a new fridge, and a new futon, i know how old these are!!! but wonderful value, as most other cottages on the beach are 2000 and up. cant wait till next time!!!

1 of 2 match: Rental types, Waterfront

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Price per night from

$339

131 North Shore Blvd Unit 7

East Sandwich apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Rental types, Waterfront

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Price per night from

$170

14 Captain Crocker

East Sandwich house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“Loved it!” We loved this house. It's right on the beach, it's private, and the sunsets are beautiful (and different each night). We loved being able to let our kids play on the beach while we watched them from the deck with our coffee. Not having to lug everything but the kitchen sink down to the beach was a huge bonus. If we needed to use the restroom, get a snack, or take a break from the sun, the house was right there. We would definitely stay here again.

1 of 2 match: Rental types, Waterfront

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Price per night from

$339

72 Salt Marsh Rd

East Sandwich house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Waterfront

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Price per night from

$428

Stunning Marsh Views, Near Pleasant Street Beach!

South Chatham house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Rental types, Waterfront

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Price per night from

$214

Rehoboth Beach - Life on the Bay

Rehoboth Beach house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Rental types, Waterfront

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Price per night from

$620

New Luxe! 9BR,7BA, Elevator, Sleeps 30, EV Charger

Lake Harmony house

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 30

1 of 2 match: Rental types, Waterfront

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Price per night from

$1,709

McGuire J 119136

Bethany Beach house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Rental types, Waterfront

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Price per night from

$612

Taggart 109490

Bethany Beach apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

1 of 2 match: Rental types, Waterfront

1 of 2 filters match

Price per night from

$598

Viewing 38 of 1,038
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