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, 346 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)

28 Nov – 5 Dec

$214 SGD per night

Guest favourite

Guest suite in Round Pond

4.79 out of 5 average rating, 107 reviews

Round Pond Crows Nest Brand new and ready for you!

Newly renovated efficiency apartment with exterior entrance. Roomy bed/living room, kitchenette, private bathroom w/ shower. Comfy bed, a table for two looking out at the big maple treetop (with a few hints of the ocean beyond), kitchenette has a bar sink, fridge for your leftovers/bevys, and a microwave to heat them up! It’s on the 3rd floor, so you’ll be getting your workout! Red chairs on the front yard are for guest use- enjoy the fresh air and ocean breeze! Very clean, bright space.

26 Sep – 3 Oct

$138 SGD per night

Guest favourite

Flat in Edgecomb

4.91 out of 5 average rating, 298 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.

15–22 Mar

$144 SGD per night

Guest favourite

Guest suite in Woolwich

4.92 out of 5 average rating, 187 reviews

Private Guest Apartment with separate entrance.

Your perfect base for discovering all the wonderful places Midcoast Maine has to offer. Located on a peaceful wooded lot, this one bedroom apartment sits on the ground floor of our 2-story home. Separate private deck entry with parking, comfortable queen bedroom, Wifi; fully equipped kitchenette; spacious bathroom with large jacuzzi tub and separate walk-in shower. Roomy sitting/dining area opens out onto deck with Adirondack chairs; table and grill. Large smart TV. Fast Wi-Fi. Firepit.

28 Jul – 4 Aug

$140 SGD per night

Guest favourite

Cottage in Boothbay Harbor

4.98 out of 5 average rating, 328 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.

12–19 Apr

$227 SGD per night

Guest favourite

Cottage in Edgecomb

4.97 out of 5 average rating, 181 reviews

Charming Cottage With Spectacular Water View

Find peace and serenity as you gaze at the glistening waters of the Sheepscot River. Our property sitting on Davis Island in Edgecomb, Maine overlooks the quaint town of Wiscasset, providing a calm atmosphere, stunning evening sunsets, and panoramic views. Located within the Sheepscot Harbour Village Resort, you are in a prime location to have access to local shops, antique markets, and restaurants. Take a stroll down to the Pier where you can experience the water up close.

25 Oct – 1 Nov

$230 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.

30 Jul – 6 Aug

$172 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 located on a country road approximately 5 miles from downtown Boothbay Harbor. The Sheepscot River, it's coves and nature trails are close by. Enjoy the beautiful 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 taking in the beautiful night sky.

14–21 Oct

$598 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.

13–20 Oct

$195 SGD per night

Guest favourite

Flat in Boothbay

4.96 out of 5 average rating, 260 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.

8–15 Nov

$92 SGD per night

Guest favourite

Home in Edgecomb

4.95 out of 5 average rating, 406 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

28 Nov – 5 Dec

$193 SGD per night

Guest favourite

Cabin in Boothbay

4.95 out of 5 average rating, 403 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 Oct

$229 SGD per night