Vacation Rentals & Cottages in Southwest Harbor

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649 cottages

Spectacular Waterfront Home - Oyster Pond 31&32

Chatham house

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Children's pool Waterfront

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Price per night from

$1,085

Bella Vista- Four Season Resort/ Delware River/Lake/Pool/Ski/Horseback-riding

Lackawaxen chalet

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Children's pool Waterfront

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Price per night from

$286

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Wyndham Long Wharf August 11th - 18th Friday to Friday only

Newport condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Waterfront, Children's pool

1 of 2 filters match

Price per night from

$327

Romantic Waterfront Artist Cottage

Truro cottage

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

1 of 2 match: Children's pool, Waterfront

1 of 2 filters match

Price per night from

$377

Test Property S2-Signup

Birch Harbor boathouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Children's pool, Waterfront

1 of 2 filters match

Price per night from

$1,030

SUMMER COTTAGE BY THE SEA

Swans Island house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Waterfront

1 of 2 filters match

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: Children's pool, Waterfront

1 of 2 filters match

Price per night from

$442

Chadwick House

Friendship house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Children's pool, Waterfront

1 of 2 filters match

Price per night from

$458

Salt Water Front South of Rt. 28 with Private Dock and Amazing Views!

Teaticket house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Waterfront

1 of 2 filters match

Price per night from

$658

Roses on the Water Beach House

Elmira cottage

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Waterfront

1 of 2 filters match

Price per night from

$400

1 of 2 match: Children's pool, Waterfront

1 of 2 filters match

Price per night from

$653

C’est La Vue

Siasconset house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Waterfront

1 of 2 filters match

Price per night from

$1,634

Waterfront Beach Home With Attached In- Law Suite

Weymouth house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Children's pool, Waterfront

1 of 2 filters match

Price per night from

$858

Oceanfront mini home, two decks, with spectacular views.

Meteghan cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Children's pool, Waterfront

1 of 2 filters match

Price per night from

$125

Experience Your Jorney with Us

Mexico house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Children's pool, Waterfront

1 of 2 filters match

Price per night from

$213

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: Children's pool, Waterfront

1 of 2 filters match

Price per night from

$340

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: Children's pool, Waterfront

1 of 2 filters match

Price per night from

$279

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: Children's pool, Waterfront

1 of 2 filters match

Price per night from

$270

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: Children's pool, Waterfront

1 of 2 filters match

Price per night from

$286

131 North Shore Blvd Unit 7

East Sandwich apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Waterfront

1 of 2 filters match

Price per night from

$170

1 White Cap Path

Sandwich apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Waterfront

1 of 2 filters match

Price per night from

$343

72 Salt Marsh Rd

East Sandwich house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Waterfront

1 of 2 filters match

Price per night from

$429

179 B North Shore Blvd

East Sandwich cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Waterfront

1 of 2 filters match

Price per night from

$214

Smith Heights Vintage Waterfront Cottages- Gooch

Eastham cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Children's pool, Waterfront

1 of 2 filters match

Price per night from

$327

Nattuary, a Nordic Spa Retreat on the Bay of Fundy

Gardner Creek guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Children's pool, Waterfront

1 of 2 filters match

Price per night from

$208

111 North Shore Blvd

East Sandwich cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Children's pool, Waterfront

1 of 2 filters match

Price per night from

$240

233 Phillips Rd

Sagamore Beach cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Children's pool, Waterfront

1 of 2 filters match

Price per night from

$250

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: Children's pool, Waterfront

1 of 2 filters match

Price per night from

$340

36 Salt Marsh Rd.

East Sandwich cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Waterfront

1 of 2 filters match

Price per night from

$250

105 North Shore Blvd - B

East Sandwich house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Waterfront

1 of 2 filters match

Price per night from

$320

Smith Heights Vintage Waterfront Cottages- McKechnie

Eastham cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Children's pool, Waterfront

1 of 2 filters match

Price per night from

$327

11 Freeman Ave

Sandwich cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Children's pool, Waterfront

1 of 2 filters match

Price per night from

$400

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: Children's pool, Waterfront

1 of 2 filters match

Price per night from

$210

5 Captain Crocker

East Sandwich cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 7

1 of 2 match: Children's pool, Waterfront

1 of 2 filters match

Price per night from

$856

Stunning Water Views Private Dock!

Eastham house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Children's pool, Waterfront

1 of 2 filters match

Price per night from

$290

Gorgeous Home near Picturesque Lt. Island!

North Eastham house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Children's pool, Waterfront

1 of 2 filters match

Price per night from

$493

Wellfleet Waterfront home on Private Beach!

Wellfleet house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Children's pool, Waterfront

1 of 2 filters match

Price per night from

$343

Waterfront, Incredible Views and Private Dock!

South Dennis house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 14

1 of 2 match: Children's pool, Waterfront

1 of 2 filters match

Price per night from

$322

Viewing 38 of 649
rentals in Southwest Harbor

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