Squirrel Island Holiday Rentals

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Holiday Rentals in Squirrel Island

Enjoyable 1-bedroom rustic cottage in Southport.

10.0 out of 10, Exceptional, (7)
Enjoyable 1-bedroom rustic cottage in Southport.

Beautiful Harbor Views Heart of Boothbay Harbor Downtown Village near all Piers

9.6 out of 10, Exceptional, (75)
"Fantastic location, owners were nearby and easy to communicate with for any questions. Perfect views and cozy apartment for our family of 3. Would definitely stay here again!"
Beautiful Harbor Views Heart of Boothbay Harbor Downtown Village near all Piers

Oceanfront Cottage w/ Deck 2 Mi to Boothbay Harbor

3.0 star property
Oceanfront Cottage w/ Deck 2 Mi to Boothbay Harbor

Tranquil Seaside Cottage with Spectacular Views, Wifi & Washer/Dryer

2.0 star property
10.0 out of 10, Exceptional, (20)
"Beautiful location, comfortable beds and wonderful linens. This place was wonderful"
Tranquil Seaside Cottage with Spectacular Views, Wifi & Washer/Dryer

A Charming Waterfront Cottage with Touches of Elegance

10.0 out of 10, Exceptional, (111)
"My husband and our 1 year old daughter had a wonderful stay. The home is close to everything and has everything you may need. Would love to stay again. "
A Charming Waterfront Cottage with Touches of Elegance

Captain's Quarters Guest Room w/Private Bath & Entrance. Best Value in Town!

7.4 out of 10, Good, (12)
"Clean, well maintained, slighly funky in an historical way . Very convenient to great breakfast spots and downtown Bath. Would stay there again."
The price is AU$256
includes taxes & fees
7 Aug - 8 Aug
Captain's Quarters Guest Room w/Private Bath & Entrance. Best Value in Town!

Beautiful Studio in downtown Boothbay Harbor

9.0 out of 10, Wonderful, (8)
"Very cozy comfortable and convenient. Every thing we needed. "
Beautiful Studio in downtown Boothbay Harbor

Oceanfront escape with deck, views of Lobster Cove & firepit - walk to town

9.6 out of 10, Exceptional, (29)
"The cabin was very clean and a nice quiet location. Had everything we needed for a comfortable stay."
Oceanfront escape with deck, views of Lobster Cove & firepit - walk to town

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

10.0 out of 10, Exceptional, (222)
"We enjoyed everything about our place!"
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

Beautiful Oceanfront House- Stunning Water Views

9.8 out of 10, Exceptional, (9)
"The Host and his wife were so pleasant and accommodating. We enjoyed watching seals, fish and birds during our visit. Highly recommend."
Beautiful Oceanfront House- Stunning Water Views

Phenomenal Home on Coast of Maine

9.0 out of 10, Wonderful, (40)
"Had a great stay. Killer views!!"
The price is AU$983
includes taxes & fees
20 Aug - 21 Aug
Phenomenal Home on Coast of Maine

Large beautiful ocean front studio with private dock

10.0 out of 10, Exceptional, (33)
"Great place to relax and watch the seagulls and heron. Quiet even though there is a building in back of the boathouse that is a rental. General store and small restaurant just down the road. The king size bed was very comfortable. The boathouse has everything you need. "
Large beautiful ocean front studio with private dock

Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach

10.0 out of 10, Exceptional, (134)
"Wonderful hosts, truly made guests feel welcomed and valued. "
The price is AU$261
includes taxes & fees
25 Aug - 26 Aug
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach

Captain's Quarters 2BR Apartment. Walk to Everything!

8.8 out of 10, Excellent, (5)
The price is AU$409
includes taxes & fees
12 Aug - 13 Aug
Captain's Quarters 2BR Apartment. Walk to Everything!

Oceanfront, dog-friendly condo with Boothbay Harbor views & prime location

9.4 out of 10, Exceptional, (16)
"Loved the location, lots of activity but also very private and relaxing. Great place, everyone was really nice and friendly"
Oceanfront, dog-friendly condo with Boothbay Harbor views & prime location

Your own private island! Rustic and close to Nature.

9.4 out of 10, Exceptional, (32)
"wonderful place, glamping, wildlife all around, you can't but enjoy the beauty of Mid Coast Maine. Thanks for sharing your island with all of us !"
Your own private island! Rustic and close to Nature.

Cozy Waterfront Cottage with Dock

10.0 out of 10, Exceptional, (2)
"My husband and I stayed at the cozy little cottage for a weekend getaway and everything about it was great. It was in the perfect location."
Cozy Waterfront Cottage with Dock

Stover's Cove Beach Coastal Retreat

9.4 out of 10, Exceptional, (31)
"We enjoyed our stay. Nice quiet area. Short walk to a small beach which was great for beach walking and scenery. House has ample parking, plenty of bedroom space and a well stocked kitchen. We had 8 adults and did not feel cramped at all. Short drive (10-15 minutes) to coffee shops, market and restaurants. Would benefit from patio and outdoor furniture to allow guests to more fully enjoy the property and surrounding scenery "
Stover's Cove Beach Coastal Retreat

Oceanfront Cabin-Castle in Maine Woods

10.0 out of 10, Exceptional, (28)
"This was exactly what we needed. Peaceful and and super unique property with an excellent view. We loved having the state park right next door! "
Oceanfront Cabin-Castle in Maine Woods

Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views

9.2 out of 10, Wonderful, (91)
"My daughter and I enjoyed our stay."
Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views
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 Squirrel Island Hotel Reviews

Frequently asked questions

Can I find holiday rentals in Squirrel Island?

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

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

Captain's Quarters Guest Room w/Private Bath & Entrance. Best Value in Town!: This holiday home rental outside of Squirrel Island comes with WiFi so that you can feel at home during your trip. Kitchen amenities include an electric kettle to make your meal-planning easier.

What can I see and do in Squirrel Island?

Explore the area and family-friendly sights such as Boothbay Railway Village, or get out into nature at a spot like Grimes Cove Beach. Cabbage Island and Burnt Island Living Lighthouse are a couple of places you'll find in the wider area.

What are holiday rentals like in Squirrel Island?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Squirrel Island. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from public hotel lifts and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for a small group gathering.