Squirrel Island vacation rentals

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Top-rated vacation rentals in Squirrel Island

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

Guest favorite

Guesthouse in South Bristol

4.98 out of 5 average rating, 342 reviews

Waterfront Guest House on the Maine Coast

Bright open four-season guest house with fantastic view of Jones Cove and the open ocean in beautiful South Bristol, Maine. The guest house offers privacy and independence. The top floor has an open space with kitchen, sleeping area with queen bed, bathroom. The ground floor has a desk, Smart TV, seating area and French doors that open onto a stone patio. Includes Kohler generator, fiber optic wifi, outdoor grill & fire pit. The water is tidal Owner lives on property (150 ft from guest house)

Jan 19 – 26

R2,926 ZAR per night
Guest favorite

Apartment in Edgecomb

4.91 out of 5 average rating, 296 reviews

Sunny Apt in Woods 10 Min to 3 Towns- Dog Friendly

Bright, cozy apartment, surrounded by deep woods, completely separate from our home, w/ its own entrance, yet we are available if you need us. Located between Boothbay, Damariscotta, & Wiscasset, 1 mile from Route 1 and 27, on 13 acres, abutting 100s of acres of preserve land - provides the best of both worlds - peaceful woods, but less than 15 minutes from restaurants, shops & activities, plus, dedicated WiFi /2 Smart TVs. While dogs are welcome we can’t host feline guests due to allergies.

Oct 21 – 28

R1,881 ZAR per night
Guest favorite

Guesthouse in Harpswell

4.95 out of 5 average rating, 428 reviews

Harpswell Studio on Waterview Property! Lobster!

Attached Cottage Style Studio! Clean, comfy, spacious, colorful and bright! Easy access to Harpswell’s 216 miles of coastline via coastal trails, lovely side roads, small beaches and preserves. Too many trails to count in the surrounding area! Fresh lobster and seafood! Two spectacular state parks with expansive beaches within a scenic 35 minute drive! Just 45 minutes (33 miles) to Coastal Maine Botanical Gardens! Saturday check-in may be available before mid June. Please message us.

Nov 5 – 12

R2,597 ZAR per night

Popular amenities for Squirrel Island vacation rentals

Other great vacation rentals in Squirrel Island

Guest favorite

Cabin in Freedom

4.9 out of 5 average rating, 288 reviews

Cozy Lakefront Cabin in Freedom, ME

Dec 4 – 11

R1,555 ZAR per night
Guest favorite

Tiny home in Dresden

4.96 out of 5 average rating, 160 reviews

Maplenook Tiny Cabin - A Cozy Woodland Oasis

Jul 15 – 22

R2,139 ZAR per night
Guest favorite

Cottage in Topsham

4.95 out of 5 average rating, 212 reviews

Cozy waterfront home on Merrymeeting Bay.

Oct 23 – 30

R3,044 ZAR per night
Guest favorite

Guest suite in Georgetown

4.97 out of 5 average rating, 320 reviews

Luxury suite, fireplace, jacuzzi

Dec 29 – Jan 5

R4,127 ZAR per night
Guest favorite

Home in Edgecomb

4.99 out of 5 average rating, 117 reviews

Cozy Lodge Meets Mid Century Hideaway

Apr 22 – 29

R3,435 ZAR per night
Guest favorite

Guest suite in Freeport

4.96 out of 5 average rating, 193 reviews

Weather's Edge, Freeport

May 30 – Jun 6

R1,657 ZAR per night
Guest favorite

Yurt in Appleton

4.96 out of 5 average rating, 221 reviews

SUMMER ROSE a Yurt for ALL Seasons

Feb 17 – 24

R3,084 ZAR per night
Guest favorite

Yurt in Chebeague Island

4.97 out of 5 average rating, 101 reviews

Yurt on Chebeague Island

Nov 22 – 29

R2,356 ZAR per night
Superhost

Apartment in Boothbay Harbor

4.79 out of 5 average rating, 134 reviews

Beautiful Studio in downtown Boothbay Harbor

Sep 22 – 29

R2,675 ZAR per night
Guest favorite

Place to stay in Owls Head

4.97 out of 5 average rating, 157 reviews

A comforting sweet off grid cabin near the beach!

Nov 11 – 18

R2,716 ZAR per night
Guest favorite

Apartment in Damariscotta

4.92 out of 5 average rating, 250 reviews

Fernald's Backside

Dec 12 – 19

R2,223 ZAR per night
Guest favorite

Cottage in Edgecomb

4.9 out of 5 average rating, 104 reviews

Spectacular Water View Cottage

Nov 7 – 14

R2,587 ZAR per night

Other great vacation rentals in Squirrel Island

Guest favorite

Guest suite in Boothbay

4.95 out of 5 average rating, 86 reviews

Linekin Guest Suite

Apr 22 – 29

R1,465 ZAR per night
Guest favorite

Apartment in Boothbay Harbor

5.0 out of 5 average rating, 60 reviews

Harbor for Two

Nov 10 – 17

R2,608 ZAR per night
Guest favorite

Tiny home in Georgetown

5.0 out of 5 average rating, 54 reviews

Studio Cabin on Pond+Near Beach+Porch+AC+FirePit

Nov 7 – 14

R2,869 ZAR per night
Guest favorite

Cottage in Boothbay

5.0 out of 5 average rating, 100 reviews

Cottage in the woods on Ocean Point

May 6 – 13

R2,701 ZAR per night
Guest favorite

Cottage in Southport

5.0 out of 5 average rating, 37 reviews

THE COVE: New England Charm / Sprinkle of Nautical

Feb 24 – Mar 3

R10,861 ZAR per night
Guest favorite

Apartment in Boothbay

5.0 out of 5 average rating, 25 reviews

The Chickadee's Nest

Oct 23 – 30

R2,733 ZAR per night
Guest favorite

Home in Boothbay Harbor

5.0 out of 5 average rating, 68 reviews

Pinkham Cove - Water Front Cottage

Mar 6 – 13

R7,156 ZAR per night
Guest favorite

Guesthouse in Brunswick

4.94 out of 5 average rating, 87 reviews

Modern Brunswick Cottage near Bowdoin & Downtown

Dec 24 – 31

R1,682 ZAR per night
Guest favorite

Cottage in Georgetown

4.98 out of 5 average rating, 98 reviews

Cottage on Todd Bay

Oct 21 – 28

R3,073 ZAR per night
Guest favorite

Home in Georgetown

5.0 out of 5 average rating, 21 reviews

Moss House: Cozy waterfront retreat w/ wood stove

Sep 11 – 18

R11,337 ZAR per night
Guest favorite

Home in Boothbay

4.97 out of 5 average rating, 35 reviews

Postcard views, ocean front and idyllic cove

Mar 12 – 19

R7,894 ZAR per night
Guest favorite

Apartment in Woolwich

5.0 out of 5 average rating, 25 reviews

Cozy, MidCoast Apartment

Jun 1 – 8

R2,626 ZAR per night

Destinations to explore

  1. Airbnb
  2. United States
  3. Maine
  4. Lincoln County
  5. Southport
  6. Squirrel Island