Squirrel Island Vacation Rentals

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Check prices for these dates

Next weekend
Aug 22 - Aug 24
In two weeks
Aug 29 - Aug 31
In one month
Sep 12 - Sep 14
In two months
Oct 10 - Oct 12

Browse Select Squirrel Island Vacation Homes

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

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

The price is CA $180
CA $276 total
includes taxes & fees
Aug 17 - Aug 18
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
Captain's Quarters Guest Room w/Private Bath & Entrance. Best Value in Town!
Property grounds

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 CA $124
CA $226 total
includes taxes & fees
Aug 20 - Aug 21
Captain's Quarters Guest Room w/Private Bath & Entrance. Best Value in Town!
Bluebird Ocean Point | Deluxe King | Private Beach + Near Grimes Cove Beach
Property grounds

Bluebird Ocean Point | Deluxe King | Private Beach + Near Grimes Cove Beach

10.0 out of 10, Exceptional, (1)
"The restaurant at the property is amazing. Loved our bartender and our waitress Emma was amazing. She went above and beyond to make our evening unforgettable. We will definitely be back My only complaint is when booking it looks like you are getting a small cabin. But they are actually normal hotel rooms. "
The price is CA $334
CA $430 total
includes taxes & fees
Sep 7 - Sep 8
Bluebird Ocean Point | Deluxe King | Private Beach + Near Grimes Cove Beach
Captain's Quarters 1BR Apartment. Walk to everything.
Property grounds

Captain's Quarters 1BR Apartment. Walk to everything.

7.8 out of 10, Good, (7)
"Very nice cozy place to make home base for a week. Had everything I needed and owner was very responsive with all of my questions. Primary destination was Bath and very convenient to everything I needed. Thank you!"
The price is CA $137
CA $240 total
includes taxes & fees
Aug 17 - Aug 18
Captain's Quarters 1BR Apartment. Walk to everything.
Laughton House @ Pemaquid Beach
Terrace/patio

Laughton House @ Pemaquid Beach

10.0 out of 10, Exceptional, (7)
"Wonderful, spacious home that has been beautifully decorated and maintained. Francine and Greg were great hosts. Will definitely be back."
The price is CA $821
CA $1,364 total
includes taxes & fees
Sep 10 - Sep 11
Laughton House @ Pemaquid Beach
Maine Coast House with Spectacular Ocean Views and Beach for Swimming
Outdoor dining

Maine Coast House with Spectacular Ocean Views and Beach for Swimming

9.4 out of 10, Exceptional, (25)
"Perfect base for exploring the mid-coast region. "
The price is CA $441
CA $892 total
includes taxes & fees
Aug 30 - Aug 31
Maine Coast House with Spectacular Ocean Views and Beach for Swimming
Welcome to Owl House - Your Coastal Retreat in East Boothbay!
Sun loungers

Welcome to Owl House - Your Coastal Retreat in East Boothbay!

10.0 out of 10, Exceptional, (5)
"Spacious and comfortable home with open floor plan. We really enjoyed our walks everyday - two blocks from crashing waves, pine trees and steps from the courts and field. It feels remote uniquely beautiful place, yet it is so convenient to stores and restaurants in Boothbay Harbor."
The price is CA $553
CA $947 total
includes taxes & fees
Aug 23 - Aug 24
Welcome to Owl House - Your Coastal Retreat in East Boothbay!
Downtown Boothbay Harbor, 2-Story Cottage
Exterior

Downtown Boothbay Harbor, 2-Story Cottage

9.4 out of 10, Exceptional, (22)
"Loved how walkable this property is! "
The price is CA $206
CA $423 total
includes taxes & fees
Sep 7 - Sep 8
Downtown Boothbay Harbor, 2-Story Cottage
Greenleaf Inn 3 - Gorgeously Renovated King Suite, Large Bath, Balcony, Harbor Views!
Property grounds

Greenleaf Inn 3 - Gorgeously Renovated King Suite, Large Bath, Balcony, Harbor Views!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Our host did a tremendous job making us feel welcome. "
The price is CA $344
CA $446 total
includes taxes & fees
Sep 3 - Sep 4
Greenleaf Inn 3 - Gorgeously Renovated King Suite, Large Bath, Balcony, Harbor Views!
Geodesic Dome w/ Riverfront Deck, Lovely Views, & High-Speed WiFi - Dogs Welcome
Property grounds

Geodesic Dome w/ Riverfront Deck, Lovely Views, & High-Speed WiFi - Dogs Welcome

9.0 out of 10, Wonderful, (61)
"We stayed in October when the trees were gorgeous and the dome house is nestled in a wooded area. So pretty! Lots of room for everyone. Wish we could have stayed longer."
The price is CA $265
CA $626 total
includes taxes & fees
Sep 15 - Sep 16
Geodesic Dome w/ Riverfront Deck, Lovely Views, & High-Speed WiFi - Dogs Welcome
Tiny A-Frame Romantic Getaway
TV

Tiny A-Frame Romantic Getaway

10.0 out of 10, Exceptional, (3)
"Very nice and very quiet "
The price is CA $632
CA $1,003 total
includes taxes & fees
Aug 19 - Aug 20
Tiny A-Frame Romantic Getaway
More then a Motel With Garden , Renovated Rooms at heart of Boothbay
Interior

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

2.0 star property
6.8 out of 10, (3)
"clean, affordable accomadations. Manager helpful and responsive"
The price is CA $460
CA $625 total
includes taxes & fees
Aug 31 - Sep 1
More then a Motel With Garden , Renovated Rooms at heart of Boothbay
Mid Coast Getaway w/ water views
TV

Mid Coast Getaway w/ water views

9.0 out of 10, Wonderful, (2)
"You couldn’t ask for a better view, it was everything we had hoped and more."
The price is CA $290
CA $479 total
includes taxes & fees
Aug 31 - Sep 1
Mid Coast Getaway w/ water views
Boothbay Harbors Ocean View Garden Suite! Admiral's Quarters Room 9 - Jersey's Favorite Room!
Smart TV, fireplace

Boothbay Harbors Ocean View Garden Suite! Admiral's Quarters Room 9 - Jersey's Favorite Room!

10.0 out of 10, Exceptional, (2)
"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 $367
CA $477 total
includes taxes & fees
Aug 24 - Aug 25
Boothbay Harbors Ocean View Garden Suite! Admiral's Quarters Room 9 - Jersey's Favorite Room!
Boothbay Harbor King Suite – Room 11 at Admiral's Quarters Inn
Smart TV, fireplace

Boothbay Harbor King Suite – Room 11 at Admiral's Quarters Inn

10.0 out of 10, Exceptional, (5)
"Our flight was delayed so we only got to enjoy this place from a quick nights sleep and morning breakfast, but we can't wait to go back. The view is so beaytiful, the host was very helpful given our late checkin, and gave us great recommendations for breakfast. Very friendly and everything you need to relax amongst the beauty of Maine."
The price is CA $402
CA $522 total
includes taxes & fees
Aug 24 - Aug 25
Boothbay Harbor King Suite – Room 11 at Admiral's Quarters Inn
Escape to Positive Outlook
Dining

Escape to Positive Outlook

The price is CA $363
CA $568 total
includes taxes & fees
Aug 26 - Aug 27
Escape to Positive Outlook
Camp Forever cottage
Outdoor dining

Camp Forever cottage

9.6 out of 10, Exceptional, (52)
"Great stay. My husband and I were there for 4 days. Peaceful and quiet. Lovely views. Just perfect for the two of us. Short drive to area sites, businesses and restaurants."
The price is CA $206
CA $395 total
includes taxes & fees
Sep 15 - Sep 16
Camp Forever cottage
Award Winning Luxury Carriage House a short stroll from town!
Fridge, microwave, oven, stovetop

Award Winning Luxury Carriage House a short stroll from town!

2.0 star property
10.0 out of 10, Exceptional, (8)
"Amazing location and beautiful little property. Everything was immaculate and welcoming, and we felt so taken care of, down to the small touches like just the coffee we like! Communication was great and timely, too. We'll definitely be back next time we are in Maine!"
The price is CA $587
CA $900 total
includes taxes & fees
Aug 20 - Aug 21
Award Winning Luxury Carriage House a short stroll from town!
Fantastic Waterfront Views
3 bedrooms, WiFi

Fantastic Waterfront Views

9.8 out of 10, Exceptional, (7)
"Our favorite part about our stay at this location was being able to look out the many sliding door windows to see the ocean view. It was a very relaxing place to stay. "
The price is CA $363
CA $604 total
includes taxes & fees
Aug 17 - Aug 18
Fantastic Waterfront Views
Orchid Harbor, Bailey Island 3BR
Interior

Orchid Harbor, Bailey Island 3BR

10.0 out of 10, Exceptional, (3)
"Orchid Harbor was perfect for my 3 week escape from life. Bailey Island is quiet and the house is comfortable and accommodating for family and friends.The outdoor seating along the ocean was our favorite place to be."
The price is CA $325
CA $691 total
includes taxes & fees
Sep 10 - Sep 11
Orchid Harbor, Bailey Island 3BR
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

Fishermans Wharf Inn

Fishermans Wharf Inn

10/10 Excellent
"It was very close to our boat trip. It was a very convenient place to stay right downtown Boothbay Harbor. "
Lorraine 2-night trip
Posted 2 days ago
Fishermans Wharf Inn