Holiday rentals in Boothbay

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Top-rated holiday rentals in Boothbay

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Guest favourite

Guest house in South Bristol

4.98 out of 5 average rating, 344 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)

30 Dec – 6 Jan

$210 SGD per night

Guest favourite

Home in Edgecomb

4.99 out of 5 average rating, 119 reviews

Cozy Lodge Meets Mid Century Hideaway

Ah where to begin with my cozy hideaway! If you're looking for a quiet & nurturing space to curl up in and be creative, relax after a day of exploring, or work remotely, this is the home for you. The house sits on 2 acres and is surrounded by trees. The upper floor features two bedrooms, both with casper mattresses, a full bath, and thirteen-foot ceilings. The design of the lower level's living space is warm and inviting; a Maine retreat close to all the amenities The Midcoast has to offer.

21–28 Apr

$219 SGD per night

Guest favourite

Flat in Edgecomb

4.91 out of 5 average rating, 297 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.

28 Oct – 4 Nov

$137 SGD per night

Guest favourite

Cottage in Boothbay Harbor

4.98 out of 5 average rating, 326 reviews

The Cottage at the McCobb House

Freshly renovated inside and out, the cottage is your private Maine camp. Located on an acre and a half of wooded grounds, and surrounded by forest, the cottage feels secluded, but it’s only a mile to the restaurants, shops, and waterfront attractions of bustling Boothbay Harbor. With hiking trails in the Pine Tree Preserve that adjoins the property and the Lobster Cove Meadow Preserve a five minute walk up the road, you can also explore nature and enjoy the solitude of the woods.

27 Feb – 6 Mar

$224 SGD per night

Guest favourite

Guest house in Georgetown

4.9 out of 5 average rating, 136 reviews

Island Alchemy Cottage

Charming cottage on a beautiful island near marina, beaches, restaurants, and hiking trails. Wonderful mid-coast Maine location for lots of possibilities for outdoor adventures, antiquing, visiting art galleries and shops, and enjoying delicious cuisine. The cottage has everything you need for a peaceful getaway. Decorated with natural elements and local art pieces to get you in the mood for this beautiful location.

16–23 Jul

$169 SGD per night

Guest favourite

Guest house in Boothbay Harbor

5.0 out of 5 average rating, 225 reviews

The Sparrow’s Nest Charming Country Cottage

The Sparrow's Nest is on a quiet country road approximately 5 miles from downtown Boothbay Harbor. The Sheepscot River, it's coves and nature trails are close by. Enjoy the beautiful and peaceful country surroundings, gardens, and the miracle of nature. What a delight to wake up to the sound of birdsong while enjoying a cup of local coffee, or sitting by the outdoor fire sipping wine and marveling at the night sky.

18–25 Sep

$592 SGD per night

Superhost

Flat in Boothbay Harbor

4.79 out of 5 average rating, 134 reviews

Beautiful Studio in downtown Boothbay Harbor

Beautiful, Large, first floor studio in downtown Boothbay Harbor. 4 minute walk to the harbor, footbridge, shops and restaurants. Located behind the Opera House. 1 queen Bed and 2 twins. Perfect for a family. Fully furnished. Two beautiful, big, bay windows, spacious and homie. Full kitchen with all pots pans and liens available. WiFi T.V. Free off street Parking for one car across the street.

21–28 Oct

$192 SGD per night

Guest favourite

Home in Lisbon

4.94 out of 5 average rating, 331 reviews

Unplug at a Beachy Bolthole with Classic New England Style

Chill on the porch after exploring a scenic local walking trail and soak up the serenity of this breezy blue and white hideaway. Striped oars, starfish, smooth shells, and ocean scenes blend with shades of teal and aqua for a thoroughly calm space. There are EV chargers behind the post office. It’s around a block and a half.

1–8 Dec

$90 SGD per night

Guest favourite

Cabin in Edgecomb

4.87 out of 5 average rating, 858 reviews

The Highland Cottage on Sheepscot

NO HIDDEN FEES THE PRICE IS THE PRICE + CLEANING! Charming, updated, 1920's cottage directly on the banks of the Sheepscot bay. Cottage has - one bedroom with queen bed, bistro table for two, sitting area with sofa and cable television, small convenience kitchen area (no stove), full bath, linens

4–11 Oct

$198 SGD per night

Guest favourite

Flat in Boothbay

4.96 out of 5 average rating, 259 reviews

Sunnymeade

Centrally located close to Boothbay Harbor, East Boothbay and Southport Island. Coastal Maine Botanical Gardens, Boothbay Region Land Trust's 26 hiking trails, Boothbay Railroad Village with live steam train rides and much, much more are great spots to visit.

17–24 Oct

$112 SGD per night

Guest favourite

Home in Edgecomb

4.95 out of 5 average rating, 402 reviews

Sheepscot Harbour Cottage/waterview

Well maintained two bedroom (K&Q) cottage/wooden beams in Sheepscot Harbour Village community. Modern large kitchen/appliances/washer/dryer, 1.5 baths, living room/fireplace, covered/screened & open porches, gorgeous gardens, sunsets & yards to river

26 Nov – 3 Dec

$194 SGD per night

Guest favourite

Cabin in Boothbay

4.95 out of 5 average rating, 402 reviews

Simple Boothbay Log Cabin on Water

Relax, reflect, & let time stand still when you visit this tiny, off-the-grid (NO ELECTRICITY) log cabin. Lobster bakes, swim, paddle the cove, swing the hammock, enjoy an hypnotic fire and unplug. Looking for pure Maine experience in the Mid-Coast?

4–11 Sep

$233 SGD per night