Vacation rentals in Cutler Harbor

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Top-rated vacation rentals in Cutler Harbor

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Home in Jonesboro, Maine

4.96 out of 5 average rating, 104 reviews

The Chandler House with private waterfront.

(Long term discounted bookings available, inquire directly.) This newly renovated 3 bedroom/2 bath home is nestled on the tidal waters of Mason's Bay. The Chandler House boasts "all brand-new everything." We took this 1940's Craftsman Style home down to its studs. Brand new kitchen with with granite counters and all new LG appliances. New washer and dryer. High speed wifi with a 55" smart TV. The large rear deck has a hot outdoor shower. Beyond the orchard is the waterfront with a firepit!

Sep 22 – 29

$99 per night
Guest favorite

Cottage in Machiasport, Maine

4.97 out of 5 average rating, 154 reviews

Cottage/w ocean view, hiking + lobster boat lounge

Overlooking Holmes Bay and lovely Long Point nature reserve, the Dock House is a stylish, mini-home connected to a lobster boat library & lounge. Enjoy sun-filled rooms and mid-century modern decor as well as access to a small beach. Hike some of Maine's best trails (minutes away) or drive to Acadia, Campobello, Eastport, the Schoodic Peninsula and much more. Visit tourist-free coastal towns or go antiquing. Buy fresh lobster, grill on the deck, or dine in-town at renowned Helen's restaurant.

Jan 26 – Feb 2

$190 per night
Guest favorite

Guest suite in St. Andrews, Canada

4.99 out of 5 average rating, 193 reviews

Homestead Cottage downtown Saint Andrews

This private newly renovated suite is perfect for 1-2 people looking to stay in the pretty seaside town of Saint Andrews. Situated away from the street, with ample parking, this suite has comfortable modern furnishings, a fully equipped kitchen and private bathroom, within a short walking distance to downtown Saint Andrews and its many amenities including restaurants, shopping, gardens, museums, walking routes, nature reserves, beaches as well as whaling and outdoor excursions. Come and stay!

Feb 25 – Mar 4

$63 per night

Popular amenities for Cutler Harbor vacation rentals

Other great vacation rentals in Cutler Harbor

Guest favorite

Cottage in Machiasport, Maine

4.96 out of 5 average rating, 77 reviews

The Maine Salt River Cottage

Dec 3 – 10

$149 per night
Guest favorite

Cottage in Whiting, Maine

4.97 out of 5 average rating, 32 reviews

Private Lakeside Cottage

Dec 13 – 20

$150 per night
Guest favorite

Cabin in East Machias, Maine

5.0 out of 5 average rating, 10 reviews

Mountain Cabin with a View in East Machias, Maine

May 29 – Jun 5

$123 per night
Guest favorite

Home in Eastport, Maine

4.95 out of 5 average rating, 20 reviews

Eagles Bluff Cottage

Feb 18 – 25

$125 per night
Guest favorite

Home in Machiasport, Maine

4.93 out of 5 average rating, 92 reviews

Cozy Cape Cod offers sweeping ocean views

Nov 26 – Dec 3

$126 per night
Guest favorite

Cottage in Machiasport, Maine

5.0 out of 5 average rating, 12 reviews

Seaclusion: Ocean-front home on Maine’s Bold Coast

Nov 29 – Dec 6

$228 per night
Superhost

Tiny home in Whiting, Maine

4.94 out of 5 average rating, 17 reviews

Little Mountain Cottage in Whiting Maine.

Aug 22 – 29

$160 per night
Guest favorite

Place to stay in Grand Manan, Canada

4.94 out of 5 average rating, 49 reviews

Aunt Sabra's Tree Point Cabin with Private Gazebo

Jun 4 – 11

$129 per night
Guest favorite

Cabin in Grand Manan, Canada

4.86 out of 5 average rating, 59 reviews

The Guillemots Nest

Jun 3 – 10

$72 per night
Guest favorite

Cottage in Grand Manan, Canada

4.96 out of 5 average rating, 25 reviews

Moody Ocean - Hot Tub, 2 Bdrm Oceanfront Cottage

Mar 4 – 11

$116 per night
Guest favorite

Campsite in Machiasport, Maine

4.93 out of 5 average rating, 43 reviews

Glamping at Bucks Harbor Maine

Jun 20 – 27

$75 per night
Guest favorite

Guesthouse in Addison, Maine

4.94 out of 5 average rating, 90 reviews

Buddy's Basin

Jul 26 – Aug 2

$71 per night

Destinations to explore

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