Holiday rentals in Squirrel Island
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Top-rated holiday rentals in Squirrel Island
Guests agree: these stays are highly rated for location, cleanliness and more.
Guest house in South Bristol
4.98 out of 5 average rating, 342 reviewsWaterfront 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)
19–26 Jan
Flat in Edgecomb
4.91 out of 5 average rating, 296 reviewsSunny 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.
21–28 Oct
Guest house in Harpswell
4.95 out of 5 average rating, 428 reviewsHarpswell 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.
5–12 Nov
Holiday rentals for every style
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Popular amenities for Squirrel Island holiday rentals
Other great holiday rentals in Squirrel Island
Guest house in Orland
4.99 out of 5 average rating, 102 reviewsCozy cottage in Orland Village-Penobscot Bay area
12–19 Feb
Cabin in Freedom
4.9 out of 5 average rating, 288 reviewsCozy Lakefront Cabin in Freedom, ME
4–11 Dec
Tiny home in Dresden
4.96 out of 5 average rating, 160 reviewsMaplenook Tiny Cabin - A Cozy Woodland Oasis
15–22 Jul
Cottage in Topsham
4.95 out of 5 average rating, 212 reviewsCozy waterfront home on Merrymeeting Bay.
23–30 Oct
Guest suite in Georgetown
4.97 out of 5 average rating, 320 reviewsLuxury suite, fireplace, jacuzzi
29 Dec – 5 Jan
Guest suite in Boothbay
4.95 out of 5 average rating, 86 reviewsLinekin Guest Suite
22–29 Apr
Flat in Boothbay Harbor
5.0 out of 5 average rating, 60 reviewsHarbor for Two
10–17 Nov
Tiny home in Georgetown
5.0 out of 5 average rating, 54 reviewsStudio Cabin on Pond+Near Beach+Porch+AC+FirePit
7–14 Nov
Cottage in Boothbay
5.0 out of 5 average rating, 100 reviewsCottage in the woods on Ocean Point
6–13 May
Cottage in Southport
5.0 out of 5 average rating, 37 reviewsTHE COVE: New England Charm / Sprinkle of Nautical
24 Feb – 3 Mar
Flat in Boothbay
5.0 out of 5 average rating, 25 reviewsThe Chickadee's Nest
23–30 Oct
Home in Boothbay Harbor
5.0 out of 5 average rating, 68 reviewsPinkham Cove - Water Front Cottage
6–13 Mar
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