Squirrel Island Vacation Rentals

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Check prices for these dates

Next weekend
Jul 25 - Jul 27
In two weeks
Aug 1 - Aug 3
In one month
Aug 15 - Aug 17
In two months
Sep 12 - Sep 14

Browse Select Squirrel Island Vacation Homes

Dog-friendly Fisher Hill home with patio and wood stove - walk to the harbor
Relax on the deck with Adirondack chairs, enjoy a cozy fireplace, and unwind in a serene natural setting.

Dog-friendly Fisher Hill home with patio and wood stove - walk to the harbor

9.6 out of 10, Exceptional, (34)
"Very clean and had everything we needed for a nice long weekend with our pup in Boothbay Harbor"
Dog-friendly Fisher Hill home with patio and wood stove - walk to the harbor
Tranquil Seaside Cottage with Spectacular Views, Wifi & Washer/Dryer
Enjoy a clean, contemporary kitchen with a large window offering a view of the surrounding landscape.

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

2.0 star property
10.0 out of 10, Exceptional, (19)
"Beautiful location, comfortable beds and wonderful linens. This place was wonderful"
Tranquil Seaside Cottage with Spectacular Views, Wifi & Washer/Dryer
Captain's House 2BR Apartment. Walk to Everything!
Property grounds

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

8.8 out of 10, Excellent, (3)
"Nice, clean, cosy, conveniently located and easy enough to find. Great communication with host, comfortable beds and plenty of hot water. very responsive and would definitely consider using again. "
The price is CA $209
CA $328 total
includes taxes & fees
Jul 20 - Jul 21
Captain's House 2BR Apartment. Walk to Everything!
1BR Guest Suite w/Private Bath & Entrance. Best Value in Town!
Property grounds

1BR Guest Suite w/Private Bath & Entrance. Best Value in Town!

7.0 out of 10, Good, (10)
"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 CA $111
CA $210 total
includes taxes & fees
Jul 21 - Jul 22
1BR Guest Suite w/Private Bath & Entrance. Best Value in Town!
NEW! Coveside! Designer decor, waterfront, AC, 2 Bedroom in Harpswell.
Fridge, microwave, oven, stovetop

NEW! Coveside! Designer decor, waterfront, AC, 2 Bedroom in Harpswell.

10.0 out of 10, Exceptional, (1)
" Absolutely SpectacularThis stunning Maine home exceeded every expectation. Waking up each morning to watch sunshine sparkle off the bay with coffee became our cherished daily ritual – there's simply no better way to start the day in this idyllic setting.The attention to detail throughout is extraordinary. Beautiful design, thoughtful decoration, and pristine cleanliness with no clutter anywhere. Super comfortable beds with the softest sheets we've experienced, luxurious towels, and perfect...
NEW! Coveside! Designer decor, waterfront, AC, 2 Bedroom in Harpswell.
Dog-friendly bay view home - water views, dock access
Enjoy cooking in this well-equipped kitchen with a granite countertop, sink, and stainless steel appliances.

Dog-friendly bay view home - water views, dock access

6.4 out of 10, (6)
"Nice and quiet. Beautiful view of the water"
Dog-friendly bay view home - water views, dock access
Well-located, dog-friendly home - walk to footbridge & Barrett Park
Enjoy cooking and dining in this well-equipped kitchen with a central island and dining area.

Well-located, dog-friendly home - walk to footbridge & Barrett Park

9.4 out of 10, Exceptional, (33)
"A nice, quiet location that is just a walk away from a pretty town, and not too far of a drive away from many great places to visit along the coastline."
Well-located, dog-friendly home - walk to footbridge & Barrett Park
Dog-friendly home with high-speed WiFi, washer/dryer, & private dock
Enjoy cooking in this well-lit kitchen with ample workspace and a large island.

Dog-friendly home with high-speed WiFi, washer/dryer, & private dock

8.6 out of 10, Excellent, (38)
"Super clean and excellent location with a view."
Dog-friendly home with high-speed WiFi, washer/dryer, & private dock
Peaceful home with forest views & great yard - minutes to town
Relax in this spacious living room with a high ceiling, large windows, and a cozy fireplace.

Peaceful home with forest views & great yard - minutes to town

8.8 out of 10, Excellent, (5)
"Your home is beautiful!! Love all the windows, very comfortable!!"
Peaceful home with forest views & great yard - minutes to town
Peaceful Maine Home w/ Patio: Ocean Inlet Getaway!
Enjoy meals in this dining area with a glass-top table and comfortable seating.

Peaceful Maine Home w/ Patio: Ocean Inlet Getaway!

10.0 out of 10, Exceptional, (13)
"Our family enjoyed our stay at this home in Bath, ME The host was very kind and helpful!"
Peaceful Maine Home w/ Patio: Ocean Inlet Getaway!
Sunny coastal retreat with deck, grill, beach, dock, & ocean access
Set amidst lush greenery, this traditional building features a gabled roof and a serene natural setting.

Sunny coastal retreat with deck, grill, beach, dock, & ocean access

9.0 out of 10, Wonderful, (8)
"Wooded setting is very nice and quiet in a well maintained house. Convenient to Boothbay Harbor, East Boothbay, and Maine Botanical Gardens. A list of nearby hiking trails would be useful. Lots of nearby restaurants. We liked Shannon's Unshelled, Thistle Inn, and Carriage House. Linekin/Burley hike was rugged but very good on Ocean Point Rd."
Sunny coastal retreat with deck, grill, beach, dock, & ocean access
Dog-friendly beach house with WiFi, private washer/dryer, deck, beautiful views
Relax in this inviting living area with a dining table for four, comfortable sofa, and armchair.

Dog-friendly beach house with WiFi, private washer/dryer, deck, beautiful views

9.6 out of 10, Exceptional, (32)
"The proximity to our activities and space for our family was perfect."
Dog-friendly beach house with WiFi, private washer/dryer, deck, beautiful views
Boothbay Harbors Garden Suite - Admiral's Quarters Room 9 - Fireplace & Stunning Harbor Views!
Relax in this serene sunroom with a stunning marina view, featuring a comfortable sofa set, wicker chairs, and a small table with a lamp.

Boothbay Harbors Garden Suite - Admiral's Quarters Room 9 - Fireplace & Stunning Harbor Views!

10.0 out of 10, Exceptional, (1)
"The greenleaf/admirals quarters was fantasic! John, was an unbelievable host. He made sure to give us a tour of the whole property, as well as made us feel welcome with an abundance of complementary items to include food and drink, as well as a bonfire at dusk with s’mores. All around fantastic experience. The room was extremely clean and comfortable and the whole place seems to have had brand new renovation. 100% recommend."
The price is CA $402
CA $522 total
includes taxes & fees
Jul 29 - Jul 30
Boothbay Harbors Garden Suite - Admiral's Quarters Room 9 - Fireplace & Stunning Harbor Views!
Swim, Kayak & Relax in Coastal Comfort from this Charming, Pet-Friendly Home
3 bedrooms, iron/ironing board, travel crib, free WiFi

Swim, Kayak & Relax in Coastal Comfort from this Charming, Pet-Friendly Home

Swim, Kayak & Relax in Coastal Comfort from this Charming, Pet-Friendly Home
Oceanfront Cabin-Castle in Maine Woods
Relax in a serene space with a comfortable seating area and a view of the surrounding forest.

Oceanfront Cabin-Castle in Maine Woods

10.0 out of 10, Exceptional, (25)
"This place was amazing and so special- incredible views, great cabin, and amazing access to the water. "
Oceanfront Cabin-Castle in Maine Woods
Beautiful Oceanfront House- Stunning Water Views
Enjoy serene views of the lake from this room's large window, featuring a tranquil forest and a dock in the distance.

Beautiful Oceanfront House- Stunning Water Views

9.6 out of 10, Exceptional, (5)
"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
Beachfront Delight with detached guesthouse, sunset views & private beach access
Outdoor dining

Beachfront Delight with detached guesthouse, sunset views & private beach access

9.6 out of 10, Exceptional, (14)
"no place is a 10 BUT 8-9 is pretty good. Great Location to relax"
Beachfront Delight with detached guesthouse, sunset views & private beach access
More then a Motel With Garden , Renovated Rooms at heart of Boothbay
Relax in a cozy room with a sofa, dining table, and flat-screen TV.

More then a Motel With Garden , Renovated Rooms at heart of Boothbay

2.0 star property
8.0 out of 10, Very good, (2)
"clean, affordable accomadations. Manager helpful and responsive"
The price is CA $456
CA $619 total
includes taxes & fees
Jul 19 - Jul 20
More then a Motel With Garden , Renovated Rooms at heart of Boothbay
Charming Boothbay Harbor cottage with partial AC, full kitchen, and sun room
Relax on the porch with two comfortable chairs and a small table amidst lush greenery.

Charming Boothbay Harbor cottage with partial AC, full kitchen, and sun room

9.2 out of 10, Wonderful, (17)
"We enjoyed all of it, it was so nice to have a separate cottage for the game room. The fire pit was a plus."
Charming Boothbay Harbor cottage with partial AC, full kitchen, and sun room
Water-view retreat with beach access, deck, grill, EV charger & lawn games
Enjoy al fresco dining and relaxation on this serene deck overlooking a peaceful body of water.

Water-view retreat with beach access, deck, grill, EV charger & lawn games

9.8 out of 10, Exceptional, (18)
"The house was fantastic. Serene, clean and beautiful setting. Would stay here again and again."
Water-view retreat with beach access, deck, grill, EV charger & lawn games
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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