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Squirrel Island Vacation Rentals

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Check prices for these dates

In two weeks
24 Jul - 26 Jul
In two months
4 Sep - 6 Sep
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Squirrel Island vacation rentals

Terrace/patio

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

Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
Boothbay
7.6 out of 10, Good, (9 reviews)
"This was perfect for our one night stay to visit the botanical gardens, it was only minutes away. Also very close to quite a few dinner and shopping options. "
United States
Nichole W.
The price is AED 403
AED 640 total
includes taxes & fees
13 Jul - 14 Jul
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
Beach nearby

Across the road from Pemaquid Beach — wooded king-bed cabin for couples

Across the road from Pemaquid Beach — wooded king-bed cabin for couples
Pemaquid Beach
10.0 out of 10, Exceptional, (22 reviews)
"The cabin was perfect; the location even better, and the hosts were everything you could wish for."
United States
Mia
The price is AED 707
AED 1,247 total
includes taxes & fees
12 Jul - 13 Jul
Across the road from Pemaquid Beach — wooded king-bed cabin for couples
House (2 Bedrooms) | Interior

1 Mi to Maine Street! Mcm-style Home in Brunswick

1 Mi to Maine Street! Mcm-style Home in Brunswick
3.0 star property
Brunswick
The price is AED 448
AED 1,076 total
includes taxes & fees
16 Jul - 17 Jul
1 Mi to Maine Street! Mcm-style Home in Brunswick
Exterior

Large suite/private bath/private entrance on quiet street near Thomas Bay

Large suite/private bath/private entrance on quiet street near Thomas Bay
Brunswick
10.0 out of 10, Exceptional, (153 reviews)
"The place was lovely, communications with the host were helpful and friendly. Dinner restaurant recommendations were great as well. "
United States
Jane T.
The price is AED 474
AED 597 total
includes taxes & fees
13 Jul - 14 Jul
Large suite/private bath/private entrance on quiet street near Thomas Bay
Outdoor dining

Happy Cottage Near Everything 11

Happy Cottage Near Everything 11
Edgecomb
6.8 out of 10, (3 reviews)
"Great quit little place, great accommodations with even better help and information about the local area."
United States
George
The price is AED 327
AED 780 total
includes taxes & fees
14 Jul - 15 Jul
Happy Cottage Near Everything 11
1 bedroom, iron/ironing board, bed sheets

Cheerful Cottage Close to Everything 12

Cheerful Cottage Close to Everything 12
Edgecomb
9.6 out of 10, Exceptional, (15 reviews)
"Great experience, great location! Would highly recommend."
United States
Lynn R.
The price is AED 367
AED 857 total
includes taxes & fees
14 Jul - 15 Jul
Cheerful Cottage Close to Everything 12
Interior

Modern style in historic building in downtown Bath

Modern style in historic building in downtown Bath
Bath
9.8 out of 10, Exceptional, (10 reviews)
"Clean comfortable and right downtown"
United States
stephen e.
The price is AED 455
AED 933 total
includes taxes & fees
28 Jul - 29 Jul
Modern style in historic building in downtown Bath
Beach nearby

Across the road from Pemaquid Beach — 2-bedroom seasonal family cottage

Across the road from Pemaquid Beach — 2-bedroom seasonal family cottage
Pemaquid Beach
9.8 out of 10, Exceptional, (6 reviews)
"Great beach cottage !"
United States
Gwen M.
The price is AED 707
AED 1,335 total
includes taxes & fees
12 Jul - 13 Jul
Across the road from Pemaquid Beach — 2-bedroom seasonal family cottage
Exterior

Westwind on Winter St - 2 bedroom townhouse apartment near downtown Topsham/Brunswick

Westwind on Winter St - 2 bedroom townhouse apartment near downtown Topsham/Brunswick
Topsham
The price is AED 397
AED 1,200 total
includes taxes & fees
13 Jul - 14 Jul
Westwind on Winter St - 2 bedroom townhouse apartment near downtown Topsham/Brunswick
TV, fireplace, books

1 Mi to Maine Street! MCM-Style Home in Brunswick

1 Mi to Maine Street! MCM-Style Home in Brunswick
Brunswick
9.4 out of 10, Exceptional, (10 reviews)
"There were a number of great details, snacks, art, pottery and the story of the house and owner (worth reading)."
United States
Seraphina E.
The price is AED 312
AED 1,105 total
includes taxes & fees
16 Jul - 17 Jul
1 Mi to Maine Street! MCM-Style Home in Brunswick
Dining

Peaceful Intown Studio ~ Walk to Shops & Dining

Peaceful Intown Studio ~ Walk to Shops & Dining
Newcastle
8.6 out of 10, Excellent, (4 reviews)
"Location was perfect and Lynn was so helpful. We’d definitely stay here again!"
United States
Caycee A.
The price is AED 661
AED 821 total
includes taxes & fees
13 Jul - 14 Jul
Peaceful Intown Studio ~ Walk to Shops & Dining
2 bedrooms, iron/ironing board, bed sheets

Cheerful Cottage with Loft 9

Cheerful Cottage with Loft 9
Edgecomb
10.0 out of 10, Exceptional, (3 reviews)
"Immaculate, very cute - “tiny cottage”We loved it!"
United States
Daniel B.
The price is AED 507
AED 1,038 total
includes taxes & fees
22 Jul - 23 Jul
Cheerful Cottage with Loft 9
Living area

Across the road from Pemaquid Beach — quiet wooded king-bed cabin

Across the road from Pemaquid Beach — quiet wooded king-bed cabin
Pemaquid Beach
9.2 out of 10, Wonderful, (5 reviews)
"Loved our stay"
United States
Jeanne
The price is AED 808
AED 1,373 total
includes taxes & fees
22 Jul - 23 Jul
Across the road from Pemaquid Beach — quiet wooded king-bed cabin
Property grounds

Captain's 1BR Apt. Experience authentic Maine. Near everything. No fees.

Captain's 1BR Apt. Experience authentic Maine. Near everything. No fees.
Bath
7.6 out of 10, Good, (14 reviews)
"We stayed for two nights. Good location."
United States
Maryanne E.
The price is AED 489
AED 613 total
includes taxes & fees
19 Jul - 20 Jul
Captain's 1BR Apt. Experience authentic Maine. Near everything. No fees.
Exterior

Spacious 1 Bedroom Cottage Close to Everything 3

Spacious 1 Bedroom Cottage Close to Everything 3
Edgecomb
9.8 out of 10, Exceptional, (17 reviews)
"Great central location"
United States
Bruce O.
The price is AED 635
AED 1,190 total
includes taxes & fees
21 Jul - 22 Jul
Spacious 1 Bedroom Cottage Close to Everything 3
Outdoor dining

Captain's Guest Room. Authenticity. Value. Near everything. No fees.

Captain's Guest Room. Authenticity. Value. Near everything. No fees.
Bath
8.2 out of 10, Very Good, (23 reviews)
"Great location and a beautiful property. Great walking/driving distance from town and the waterfront, we had a great stay and would do it again! "
United States
Nina P.
The price is AED 477
AED 601 total
includes taxes & fees
2 Aug - 3 Aug
Captain's Guest Room. Authenticity. Value. Near everything. No fees.
Interior

Unique ISLAND Living off the grid -Waterfront cottage

Unique ISLAND Living off the grid -Waterfront cottage
Friendship
10.0 out of 10, Exceptional, (28 reviews)
"We love coming here and once again we had a wonderful week! The outside world melts away when you’re on Friendship Long Island."
United States
Cheryl C.
The price is AED 1,010
AED 1,830 total
includes taxes & fees
4 Aug - 5 Aug
Unique ISLAND Living off the grid -Waterfront cottage
Terrace/patio

Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (59 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
The price is AED 771
AED 1,341 total
includes taxes & fees
13 Jul - 14 Jul
Camp Forever cottage
Interior

Little Lincoln beautiful home

Little Lincoln beautiful home
Brunswick
9.2 out of 10, Wonderful, (17 reviews)
"The host was very welcoming and responsive when we had a question. We would stay here again when we come back to Brunswick. "
United States
Michael S.
The price is AED 606
AED 1,297 total
includes taxes & fees
14 Jul - 15 Jul
Little Lincoln beautiful home
Exterior detail

Tiny A-Frame Romantic Getaway

Tiny A-Frame Romantic Getaway
Wiscasset
9.8 out of 10, Exceptional, (6 reviews)
"Very nice and very quiet "
United States
justin s.
The price is AED 848
AED 1,738 total
includes taxes & fees
12 Jul - 13 Jul
Tiny A-Frame Romantic Getaway
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

Smuggler's Cove Inn

Smuggler's Cove Inn

10/10 Excellent
"We had a wonderful stay at Smuggler's Cove! We saw a beautiful sunset by the water, our room was very clean and comfortable, and everyone made us feel welcome. Shane, the bartender, was awesome, and Kash, the manager, was incredibly friendly and took the time to share the history of the inn and the local area. It made our stay even more special. We'd definitely come back!"
Soong Ting 2-night trip
Posted 2 hours ago
Smuggler's Cove Inn

Frequently asked questions

Can I find vacation rentals in Squirrel Island?

Yes, we have vacation rentals close to the most popular local attractions in Squirrel Island, or you can go with a more secluded option if you want a relaxing place to stay.

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

Smuggler's Retreat ExploreTrails, Botanic Gardens, Kayak and MORE: This vacation home rental near Squirrel Island is located on a river and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You can relax into your vacation with a garden and a selection of games.

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 Boothbay Harbor Marina are a couple of places you'll find in the larger area.

What are vacation rentals like in Squirrel Island?

Vacation rentals are private properties you can book for a couple of days or more in Squirrel Island. Vacation rentals feature amenities like laundry facilities and kitchens so you'll have everything you want. If you're concerned about a clean environment, a vacation rental can offer a sense of security away from public hotel elevators and busy front desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for families.