Squirrel Island Holiday Rentals

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Our top choices for Squirrel Island holiday rentals

10.0 out of 10, Exceptional, (1)
"This efficiency apartment was nicely furnished with everything needed and conveniently located on the main road into Boothbay Harbor. The host was generous and accommodating. The region is fun to visit!"
United States
Mary D.
The price is NZ$480
includes taxes & fees
13 Dec - 14 Dec
Queen non smoking efficiency, free parking in beautiful Boothbay,Maine.
10.0 out of 10, Exceptional, (8)
"Clean comfortable and right downtown"
United States
stephen e.
The price is NZ$380
includes taxes & fees
12 Dec - 13 Dec
Modern style in historic building in downtown Bath
10.0 out of 10, Exceptional, (144)
"Lovely space, comfortable bed, very convenient to downtown Brunswick."
United States
Kimberly G.
The price is NZ$206
includes taxes & fees
22 Dec - 23 Dec
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach
10.0 out of 10, Exceptional, (1)
"Pet friendly place and good spot! Would stay again "
United States
Shiloh F.
The price is NZ$415
includes taxes & fees
12 Dec - 13 Dec
Lovely 2-bedroom apartment with AC in charming Topsham. Close to everything!
10.0 out of 10, Exceptional, (10)
"Great location, great view, great house, great time"
United States
Carol P.
The price is NZ$2,037
includes taxes & fees
12 Dec - 13 Dec
Charming Sheepscot Overlook Cottage
9.0 out of 10, Wonderful, (2)
"Off the beaten path, easy access to beach and Spinneys"
United States
Sean B.
The price is NZ$420
includes taxes & fees
8 Jan - 9 Jan 2026
Fred Cottage - Spacious retreat on Popham Beach!
10.0 out of 10, Exceptional, (9)
"An exceptional property and guest. Would love to stay again next time Thank you Jared and Heather!"
United States
Ronald H.
The price is NZ$1,113
includes taxes & fees
13 Dec - 14 Dec
Award Winning Luxury Carriage House a short stroll from town!
9.6 out of 10, Exceptional, (9)
"We had a good time in Brunswick.... great location and jumping off point to explore."
United States
Karin S.
The price is NZ$581
includes taxes & fees
15 Dec - 16 Dec
Classic New England 1st Floor 3 BR Downtown Brunswick

Holiday Home in West Point

Escape to Positive Outlook
10.0 out of 10, Exceptional, (2)
"Place was clean, beautiful and the photos do not do it justice. The perfect get away vacation from the rat race."
United States
Gregory M.
The price is NZ$347
includes taxes & fees
15 Dec - 16 Dec
Escape to Positive Outlook

Holiday Home in Pemaquid Beach

Laughton House @ Pemaquid Beach
10.0 out of 10, Exceptional, (8)
"This house is in a great location. We could walk to the beach, or to Fort Henry to let my grandsons run around. The house is lovely and had everything we needed. We have come to this area of Maine since 2017, and this had been our favorite place to stay! "
United States
Dawn W.
The price is NZ$1,179
includes taxes & fees
23 Dec - 24 Dec
Laughton House @ Pemaquid Beach
9.8 out of 10, Exceptional, (7)
"Managers were very responsive and helpful. Condo was very clean and comfortable and close to the town of Boothbay Harbor and Ocean Point and the Botanic Gardens. "
United States
Linda O.
The price is NZ$517
includes taxes & fees
17 Dec - 18 Dec
Solitude @ The Offshore House

Apartment in Brunswick

Little Lincoln beautiful home
9.0 out of 10, Wonderful, (14)
"Simon was very easy to communicate with, the place was clean, the bed was quite comfortable, and we were right by Main Street in Brunswick which made for easy access to food and things to do. Wonderful place to stay!"
United States
Jessica B.
The price is NZ$442
includes taxes & fees
14 Dec - 15 Dec
Little Lincoln beautiful home
10.0 out of 10, Exceptional, (20)
"Beautiful place, had everything we needed!"
United States
Kathy H.
The price is NZ$860
includes taxes & fees
12 Dec - 13 Dec
Shipbuilder's Retreat, Unit 2, Sleeps 6, 5 minutes to Harbor
9.4 out of 10, Exceptional, (27)
"Perfect base for exploring the mid-coast region. "
United States
Rebecca M.
The price is NZ$830
includes taxes & fees
14 Dec - 15 Dec
Maine Coast House with Spectacular Ocean Views and Beach for Swimming
7.8 out of 10, Good, (7)
"Affordable and quiet location that felt safe and is conveniently close to Boothbay Harbor & surrounding attractions. "
United States
Melanie L.
The price is NZ$344
includes taxes & fees
12 Dec - 13 Dec
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
10.0 out of 10, Exceptional, (2)
"This was a last minute booking for our family as we had a basketball tournament, there were 8 of us including 3 children. This was the most kid friendly house we have stayed in! It was so well stocked for the entire family. The house was meticulously cleaned and the hosts were very responsive to any questions! "
United States
Melissa L.
The price is NZ$1,171
includes taxes & fees
14 Dec - 15 Dec
Pemaquid Escape | Curated Comfort + Hot Tub
9.6 out of 10, Exceptional, (18)
"Stayed here while visiting Bowdoin. Great place!"
United States
Deborah B.
The price is NZ$553
includes taxes & fees
15 Dec - 16 Dec
Vacation Creation Downtown Brunswick 2King Beds
8.4 out of 10, Very good, (10)
"Small place in a great location. Easily walk to several shops and restaurants. "
United States
Jillian B.
The price is NZ$405
includes taxes & fees
17 Dec - 18 Dec
2King Bed BR Private Apt Downtown Brunswick
10.0 out of 10, Exceptional, (46)
"Quiet and peaceful. Location was close to everything we had on our agenda. We highly recommend this as great place to stay!"
United States
Malinda E.
The price is NZ$862
includes taxes & fees
19 Dec - 20 Dec
Shipbuilder’s Retreat sleeps 6, 5 minutes to Harbor
2.0 star property
The price is NZ$286
includes taxes & fees
12 Dec - 13 Dec
Peaceful Intown Studio ~ Walk to Shops & Dining
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

Find out more about Squirrel Island

Everything you need to know about Squirrel Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Squirrel Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Squirrel Island holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Squirrel Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Squirrel Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Squirrel Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Squirrel Island holiday rentals we have selected for you start as low as NZ$344 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Squirrel Island rentals

At Expedia, we put the best Squirrel Island holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Squirrel Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Squirrel Island holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Squirrel Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Oceanfront Cabin-Castle in Maine Woods: This holiday home rental outside of Squirrel Island is located by the ocean, and has a fireplace, a selection of games and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

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 Cabbage Island. Burnt Island Living Lighthouse and Boothbay Harbor Marina 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.