A coastal landscape with a white house, a large tree, and a rocky outcrop in the distance.

Monhegan Island Holiday Rentals

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Our top choices for Monhegan Island holiday rentals

1. Shipbuilder's Retreat, Unit 2, Sleeps 6, 5 minutes to Harbor

Shipbuilder's Retreat, Unit 2, Sleeps 6, 5 minutes to Harbor
East Boothbay
10.0 out of 10, Exceptional, (32 reviews)
"Close enough to BoothBay Harbour and Botanical Gardens but private and quiet get away. Very comfortable! Spacious, good appliances and bedding. I would guess very new. Loved it!"
United States
Judith
The price is NZ$905
includes taxes & fees
14 Sept - 15 Sept
Shipbuilder's Retreat, Unit 2, Sleeps 6, 5 minutes to Harbor

2. Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything

Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
Boothbay
7.8 out of 10, Good, (10 reviews)
"Great stay! Pet friendly, super responsive host and excellent location!"
United States
Cassie M.
The price is NZ$342
includes taxes & fees
16 Aug - 17 Aug
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything

3. Shipbuilder’s Retreat sleeps 6, 5 minutes to Harbor

Shipbuilder’s Retreat sleeps 6, 5 minutes to Harbor
East Boothbay
10.0 out of 10, Exceptional, (56 reviews)
"Excellent, clean property. "
United States
Andy H.
The price is NZ$1,029
includes taxes & fees
20 Aug - 21 Aug
Shipbuilder’s Retreat sleeps 6, 5 minutes to Harbor

4. Luxury Yurt at Seaside Farm in Friendship

Luxury Yurt at Seaside Farm in Friendship
Friendship
The price is NZ$1,162
includes taxes & fees
9 Sept - 10 Sept
Luxury Yurt at Seaside Farm in Friendship

5. Newly renovated motel garden rooms heart of boothbay affordable great hospitaliy

Newly renovated motel garden rooms heart of boothbay affordable great hospitaliy
Boothbay
6.0 out of 10, (5 reviews)
"It had a very homey feel, was nice to stay at for the night and wasn’t far from town."
United States
Audreyana P.
The price is NZ$342
includes taxes & fees
1 Sept - 2 Sept
Newly renovated motel garden rooms heart of boothbay affordable great hospitaliy

6. Newly Renovated Cozy Cove Cabin at White Anchor Inn

Newly Renovated Cozy Cove Cabin at White Anchor Inn
Boothbay
8.6 out of 10, Excellent, (8 reviews)
"As advertised, comfy bed cozy cabin. Would stay again "
United States
Joseph B.
The price is NZ$379
includes taxes & fees
1 Sept - 2 Sept
Newly Renovated Cozy Cove Cabin at White Anchor Inn

7. Boothbay Harbor, 2-Story Cottage, downtown

Boothbay Harbor, 2-Story Cottage, downtown
Boothbay Harbor
9.4 out of 10, Exceptional, (29 reviews)
"Enjoyed the place, great location. "
United States
Erik P.
The price is NZ$708
includes taxes & fees
19 Aug - 20 Aug
Boothbay Harbor, 2-Story Cottage, downtown

8. Renovated The Driftwood Cabin at White Anchor Inn

Renovated The Driftwood Cabin at White Anchor Inn
Boothbay
8.8 out of 10, Excellent, (3 reviews)
"Communication with Property Owner was excellent. This cute little cottage has been renovated and has a nice feel indoors. There is a beautiful porch on the back with a lovely view. The unit includes a mini fridge and mini microwave along with a little table and two chairs. If you have long hair, water pressure could be a concern. My shower worked great but the sink water pressure was not strong. The bed was comfortable and the decor was nice. The air conditioning works fine."
United States
Abra H.
The price is NZ$396
includes taxes & fees
25 Aug - 26 Aug
Renovated The Driftwood Cabin at White Anchor Inn

9. Modern Cape -3 Bedroom- Boothbay Harbor - Near Ocean -Golf-Botanical Gardens

Modern Cape -3 Bedroom- Boothbay Harbor - Near Ocean -Golf-Botanical Gardens
Boothbay Harbor
10.0 out of 10, Exceptional, (4 reviews)
"The house was very charming, very clean & perfectly located to trails, botanical gardens, train museum & harbor! The house had everything that you could possibly need & we especially enjoyed the fire pit multiple nights!"
United States
Sharon H.
The price is NZ$1,065
includes taxes & fees
1 Sept - 2 Sept
Modern Cape -3 Bedroom- Boothbay Harbor - Near Ocean -Golf-Botanical Gardens

10. Harold Room 8 | 2 Queens + Gable Windows

Harold Room 8 | 2 Queens + Gable Windows
Boothbay Harbor
The price is NZ$808
includes taxes & fees
30 Aug - 31 Aug
Harold Room 8 | 2 Queens + Gable Windows

11. Pelican Cottage | 2 BR + Waterfront Porch

Pelican Cottage | 2 BR + Waterfront Porch
Boothbay Harbor
The price is NZ$1,519
includes taxes & fees
7 Sept - 8 Sept
Pelican Cottage | 2 BR + Waterfront Porch

12. Boothbay Harbor, The Francis Greene House, downtown

Boothbay Harbor, The Francis Greene House, downtown
Boothbay Harbor
9.4 out of 10, Exceptional, (48 reviews)
"We spent three nights at this location, which is just a short walk from the commercial area of Boothbay Harbor. In addition to restaurants in town it is only minutes away from Robinson's Wharf, which had some of the best food we experienced in 14 days of travel - definitely the best lobster. The house was as advertised and suited our needs well."
United States
Terry F.
The price is NZ$1,212
includes taxes & fees
5 Sept - 6 Sept
Boothbay Harbor, The Francis Greene House, downtown

13. Walk-to-Town Boothbay Harbor Retreat | Harbor Views | A/C | Parking| Pet Friendly

Walk-to-Town Boothbay Harbor Retreat | Harbor Views | A/C | Parking| Pet Friendly
Boothbay Harbor
6.0 out of 10, (1 review)
"Ok Beautiful location price was on the high side but very clean and state of the art."
United States
Steve R.
The price is NZ$1,338
includes taxes & fees
29 Aug - 30 Aug
Walk-to-Town Boothbay Harbor Retreat | Harbor Views | A/C | Parking| Pet Friendly

14. Oriole Suite | Stone Fireplace + Woodland

Oriole Suite | Stone Fireplace + Woodland
Boothbay Harbor
The price is NZ$1,299
includes taxes & fees
14 Sept - 15 Sept
Oriole Suite | Stone Fireplace + Woodland

15. Pemaquid Escape | Curated Comfort + Hot Tub

Pemaquid Escape | Curated Comfort + Hot Tub
Walpole
10.0 out of 10, Exceptional, (4 reviews)
"The place was beautiful, with charming and had perfect design choices. Check in was so convenient, and the hosts were quite responsive to any needs. We all felt so comfortable there. It felt private, yet was conveniently located to Damariscotta. I would absolutely rent here again."
United States
Tera P.
The price is NZ$2,044
includes taxes & fees
19 Aug - 20 Aug
Pemaquid Escape | Curated Comfort + Hot Tub

16. Druce Room 1 | Ocean Deck + French Doors

Druce Room 1 | Ocean Deck + French Doors
Boothbay Harbor
The price is NZ$1,008
includes taxes & fees
30 Aug - 31 Aug
Druce Room 1 | Ocean Deck + French Doors

17. Crow's Nest | Panoramic Ocean Views - Queen

Crow's Nest | Panoramic Ocean Views - Queen
Boothbay Harbor
The price is NZ$1,039
includes taxes & fees
31 Aug - 1 Sept
Crow's Nest | Panoramic Ocean Views - Queen

18. Sunset A | Oceanfront King + Gas Fireplace

Sunset A | Oceanfront King + Gas Fireplace
Boothbay Harbor
Sunset A | Oceanfront King + Gas Fireplace

19. Windward Suite | Harbor View + Enclosed Porch

Windward Suite | Harbor View + Enclosed Porch
Boothbay Harbor
The price is NZ$1,382
includes taxes & fees
9 Sept - 10 Sept
Windward Suite | Harbor View + Enclosed Porch

20. Admiral's Quarters | Harbor Views + Private Deck

Admiral's Quarters | Harbor Views + Private Deck
Boothbay Harbor
The price is NZ$1,261
includes taxes & fees
2 Sept - 3 Sept
Admiral's Quarters | Harbor Views + Private Deck
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Monhegan Island Hotel Reviews

Find out more about Monhegan Island

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Monhegan Island holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Monhegan Island. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Monhegan Island. Seeing all the best attractions is bound to make you fall in love with Monhegan Island. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Monhegan Island short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Monhegan Island?

Yes, there are holiday rentals close to the most popular sights in Monhegan Island, or you can select a more secluded option if you're looking for a relaxing stay. Monhegan Island is known for its art.

What are some of the best holiday rentals that Monhegan Island has to offer?

Monhegan Island Retreat - Spacious with 4 bedrooms and gorgeous ocean views.
: This highly rated holiday home rental in Monhegan Island offers a fireplace, a balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. You can relax into your holiday with a private garden and a library.

How many holiday rentals are there in Monhegan Island?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Monhegan Island stay.

What’s there to see and do in Monhegan Island?

Fish Beach and Cathedral Woods are a couple of scenic spots to enjoy the outdoors, whereas Lupine Gallery is one of the cultural attractions. Other places in town to visit include Monhegan Museum of Art & History and White Head Trail.

What’s a holiday rental in Monhegan Island like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Monhegan Island. Holiday rentals offer amenities like laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from public hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for small groups.