Vacation Rentals & Cottages in Southwest Harbor

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379 cottages

Berkshires: Romantic Cottage with spectacular view

Great Barrington cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

“A Real Gem!!!” This cottage is the perfect place for two people. It is truly as beautiful as the pictures! The pool and grounds are exceptional and the view is breathtaking. The place is extremely well maintained and the owner is very kind and helpful. We had a fabulous weekend here and would gladly return!

Match: Shared outdoor pool (unheated) Pets

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Price per night from

$274

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Seaside Vacation at Hotel Paulin

Caraquet penthouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Shared outdoor pool (unheated), Pets

1 of 2 filters match

Price per night from

$158

Casual lux near Hermitage Club & Four Columns Inn

South Newfane villa

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 8

1 of 2 match: Shared outdoor pool (unheated), Pets

1 of 2 filters match

Price per night from

$1,718

Romantic getaway with Spa treatments

Milford house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Shared outdoor pool (unheated), Pets

1 of 2 filters match

Price per night from

$201

Sweetheart Beach, HotTub, Lake-Hike, Kayak, Relax!

Caroga Lake house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Sweetheart was AWESOME” Sweetheart did not disappoint! It was a perfect place to go and "disconnect" and yet still close enough to fulfill any needs from the "real world". We enjoyed the small lake side location for walks with our dog, the hot tub for relaxing afternoon soak, the "retro Atari" gaming system and collection of board games for night time activities, and the over all peace and serenity was just what was needed for a break from the "rat race" of everyday life. Thanks to Aimee and Michael for your attention to detail for the decorations and materials provided to enhance our stay.

1 of 2 match: Shared outdoor pool (unheated), Pets

1 of 2 filters match

Price per night from

$172

GREAT VACATION HOUSE-GREAT LOCATION TO SOUTH BEACH

Edgartown house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Shared outdoor pool (unheated), Pets

1 of 2 filters match

Price per night from

$344

Cliff-perched Home with Breathtaking Ocean Views

Machiasport cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared outdoor pool (unheated), Pets

1 of 2 filters match

Price per night from

$401

Vacation Home Away from Home!

Truro house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

1 of 2 match: Shared outdoor pool (unheated), Pets

1 of 2 filters match

Price per night from

$295

Shady Harbor - Quonnie Pond and Weekapaug Beach

Charlestown house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Shared outdoor pool (unheated), Pets

1 of 2 filters match

Price per night from

$573

Brookhouse: A Cottage by the Sea

Prospect Harbor cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Shared outdoor pool (unheated), Pets

1 of 2 filters match

Price per night from

$196

Idyllic New England Farm Home Retreat

Lebanon house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Shared outdoor pool (unheated), Pets

1 of 2 filters match

Price per night from

$287

Gorgeous 1 Bed 1 Bath

Wilmington apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Shared outdoor pool (unheated), Pets

1 of 2 filters match

Price per night from

$172

2 bedroom house on private road...walk to shops

North Conway house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 8

“Very relaxing” Stayed here for two nights with my sister, nephew and his wife. Very comfortable furniture and beds.The porch was our favorite spot to sit looking over the mountains. Enjoyed our morning coffee out there. Nanci was very kind and available if we needed anything, which we did not. The place is very well stocked. I could easily stay a week here, cooking meals, hiking,watching the sun set, relaxing, and of course shopping. Love the fact that it was a stable/barn. Love the uniqueness of it. Thanks Nanci!

1 of 2 match: Shared outdoor pool (unheated), Pets

1 of 2 filters match

Price per night from

$258

New Test Property - NOT FOR RENT

Fall River apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 2 match: Shared outdoor pool (unheated), Pets

1 of 2 filters match

Price per night from

$3

Superb Location on Quiet Laneway

Little Compton house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Shared outdoor pool (unheated), Pets

1 of 2 filters match

Price per night from

$533

Dionis in Nantucket Luxury Waterfront Home

Nantucket house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Paradise” We were in heaven! This property is secluded and beyond peaceful. The house looks out on a small harbor and quiet beach with rare birds. The sunsets are extraordinary and we enjoyed many nights lounging on the porch, drinking wine, nibbling cheese or grilling (freshly caught!) fish and watching the sky turn colors before it got dark (and then we were faced with brilliant stars--we're New Yorkers so we don't get night skies like this!) The house is spacious, yet very cozy. The master bedroom has an amazing (huge!) shower and jacuzzi. The living room has big comfy couches, throw pillows and a working fireplace. One night we roasted marshmallows and played cards. A perfect stay-in evening. I feel I should also say--this house is stocked! The kitchen comes with everything you could want if you're a foodie (we grilled, made mixed drinks, made sushi one night, baked muffins, everything.) There is great cable including HBO and a video library, as well as games for kids if you should need. We loved to bike some days to a nearby beach (Madaket, about 15 minutes away) where there was a little more action than our private one (a taco restaurant called The Westender and spot with bigger surf where we went to boogie board.) The house has beach balls, paddle ball, and buckets for building sand castles. The bikes provided by owners are in great shape and there were also helmets available. Additionally, we loved that there were ocean kayaks, though we didn't have a chance to use them. Mostly, I think we all appreciated that we could completely unwind in this peaceful spot, read, sleep in, enjoy the beauty of the island, etc., but also get into town quickly if we wanted to go out for dinner or get drinks. Getting to Cisco is also a pretty quick trip--and we went twice to the brewery to get a drink after the beach and listen to live music. Overall, this was one of my best vacations in recent memory. You must try this part of the island and

1 of 2 match: Shared outdoor pool (unheated), Pets

1 of 2 filters match

Price per night from

$2,634

1 of 2 match: Shared outdoor pool (unheated), Pets

1 of 2 filters match

Price per night from

$103

Go Rustic! The Annex at Catamount Loj

Pottersville cottage

  • 4 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared outdoor pool (unheated), Pets

1 of 2 filters match

Price per night from

$178

Vacation Home on 10 Acres with Pool and Spa

Stockbridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared outdoor pool (unheated), Pets

1 of 2 filters match

Price per night from

$859

Stowe Vermont Winter Season Rental

Stowe house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

1 of 2 match: Shared outdoor pool (unheated), Pets

1 of 2 filters match

Price per night from

$859

Fabulous Post & Beam Berkshire Rental

Monterey house

  • 2 bathrooms
  • sleeps 7

1 of 2 match: Shared outdoor pool (unheated), Pets

1 of 2 filters match

Price per night from

$205

Cottonwood Cove Cottage 1 On Lake Champlain

Saint Albans cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 45 minutes

1 of 2 match: Shared outdoor pool (unheated), Pets

1 of 2 filters match

Price per night from

$161

34 Pleasant Street Lubec, ME

Lubec cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Shared outdoor pool (unheated), Pets

1 of 2 filters match

Price per night from

$281

60 Billingsgate Avenue 122925

Eastham house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Shared outdoor pool (unheated), Pets

1 of 2 filters match

Price per night from

$214

Cozy Log Cabin

Durham log cabin

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 2 hours 10 minutes

1 of 2 match: Shared outdoor pool (unheated), Pets

1 of 2 filters match

Price per night from

$235

Hotel Paulin Seaside Extended Stay Vacations

Caraquet penthouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Shared outdoor pool (unheated), Pets

1 of 2 filters match

Price per night from

$158

Cozy Beach Home - Walk Everywhere Beach and Fun!

South Yarmouth townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Shared outdoor pool (unheated), Pets

1 of 2 filters match

Price per night from

$115

Classic Cottage, walk to Private Beach/ Wiley Park

Eastham house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Shared outdoor pool (unheated), Pets

1 of 2 filters match

Price per night from

$320

Riverside Cottage

Bonshaw cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

“Would recommend to anyone with no hesitation - excellent vacation in PEI” Every day spent in Bonshaw was excellent. Hiking trails are wonderful. River closeby for canoeing and kayaking. Such a beautiful place to enjoy nature. The owners were warm and welcoming and the cottage was beautiful and very very clean. Cozy cottage with view of nature. Close to everything, especially beautiful beaches. If we have the opportunity, we would love to go again!

1 of 2 match: Shared outdoor pool (unheated), Pets

1 of 2 filters match

Price per night from

$117

Handmade House on 70 secluded acres

Cobleskill house

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 2 match: Shared outdoor pool (unheated), Pets

1 of 2 filters match

Price per night from

$166

The Perfect Vermont Experience for All Seasons

Dorset house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Shared outdoor pool (unheated), Pets

1 of 2 filters match

Price per night from

$287

Windham Cabin

Lexington log cabin

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Shared outdoor pool (unheated), Pets

1 of 2 filters match

Price per night from

$172

Bay of Fundy Seaside Cottage

Chance Harbour cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Responds fast! avg. 2 hours 16 minutes

1 of 2 match: Shared outdoor pool (unheated), Pets

1 of 2 filters match

Price per night from

$155

Stunning Vacation Country & Ski House

Woodstock house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

1 of 2 match: Shared outdoor pool (unheated), Pets

1 of 2 filters match

Price per night from

$630

Prana Residence - Spa

Cornwall Bridge house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Shared outdoor pool (unheated), Pets

1 of 2 filters match

Price per night from

$859

Former Chatham Bed and Breakfast

Chatham b&b

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

“Classic cape cod experience” Beautiful property well located on the cape non commercial sector. Tastefully appointed overall fantastic.

1 of 2 match: Shared outdoor pool (unheated), Pets

1 of 2 filters match

Price per night from

$638

Unique & Private 3 Bedroom Brewster Home

Brewster house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Shared outdoor pool (unheated), Pets

1 of 2 filters match

Price per night from

$328

The Stone House: A Quiet Lakefront Respite

Star Lake house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

1 of 2 match: Shared outdoor pool (unheated), Pets

1 of 2 filters match

Price per night from

$287

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rentals in Southwest Harbor

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