Squirrel Island holiday rentals

We found 743 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Squirrel Island that are perfect for your trip. Whether you're travelling with your children and pets, with friends or just your children, holiday homes have the best amenities for hanging out with the people that matter most, which might include a garden and hot tub. You'll be able to choose a property to rent for everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Squirrel Island

Showing deals for:8 Jan - 15 Jan

Celebrate Christmas here with your family.
Living area
Interior
Living area
Exceptional
(55 reviews)

Driftwood Beachfront Luxury Home Magnificent Ocean Views

Phippsburg

8% off
AU$10,198
for 7 nights, 1 home
AU$1,457 per night
includes taxes & fees
Driftwood Beachfront Luxury Home Magnificent Ocean Views
Exterior detail
Exterior
Living area
Room
Exceptional
(10 reviews)

Quiet waterfront serenity awaits!

Georgetown

8% off
AU$5,182
for 7 nights, 1 home
AU$740 per night
includes taxes & fees
Quiet waterfront serenity awaits!
Upstairs balcony entry third bedroom
Mossy Glen Lodge - entire lodge is your private secluded hideaway
Kitchen area, dishwasher,cooking area, and bar counter
Christmas look at Mossy Glenn Lodge
Exceptional
(23 reviews)

Mossy Glen Lodge 'Log Cabin' with a tiny brook and hammock

Boothbay

13% off
AU$3,224
for 7 nights, 1 room
AU$461 per night
includes taxes & fees
Mossy Glen Lodge 'Log Cabin' with a tiny brook and hammock
Upstairs master bedroom view
Outdoor dining
Front yard
Exterior
Exceptional
(38 reviews)

Enjoy spectacular views of Lobster Cove. Large yard, EV charger & dog friendly.

Boothbay Harbor

8% off
AU$3,912
for 7 nights, 1 home
AU$559 per night
includes taxes & fees
Enjoy spectacular views of Lobster Cove. Large yard, EV charger & dog friendly.
The large lawns allow for many outdoor gatherings too!
Sea-air nourishes our flowerbox blossoms all summer--
Charming on your arrival...
Settle & relax on the deck, flagstone patio, or 'round the fire pit--
Exceptional
(97 reviews)

Slow Down & Go Back in Time-Relax Completely in Our Maine Home

New Harbor

7% off
AU$2,046
for 7 nights, 1 home
AU$292 per night
includes taxes & fees
Slow Down & Go Back in Time-Relax Completely in Our Maine Home
Living area
Exterior
Back deck and screen porch
Screen porch
Exceptional
(9 reviews)

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

East Boothbay

8% off
AU$4,091
for 7 nights, 1 home
AU$584 per night
includes taxes & fees
Welcome to Owl House - Your Coastal Retreat in East Boothbay!
Kitchen
Living room
Back Bay Cottage, next to the Chowder House in downtown Boothbay Harbor
Kitchen
Exceptional
(77 reviews)

Year Round Luxury Waterfront Condo, Heart of Boothbay Harbor

Boothbay Harbor

12% off
AU$3,372
for 7 nights, 1 apartment
AU$482 per night
includes taxes & fees
Year Round Luxury Waterfront Condo, Heart of Boothbay Harbor
Living room.
Aerial view of condo on the left side.
Living room to kitchen.
Kitchen with granite counter top and high top seating.
Exceptional
(9 reviews)

Beautiful Condo on Ocean Cove - Easy walk to harbor-side town

Boothbay Harbor

8% off
AU$4,545
for 7 nights, 1 apartment
AU$649 per night
includes taxes & fees
Beautiful Condo on Ocean Cove - Easy walk to harbor-side town

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Book a holiday rental for your Squirrel Island getaway

Learn about the unique charm of Squirrel Island with a stay in a holiday home rental. This city has something for everyone. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in Squirrel Island

Are you hoping to find top things to see and do while you're in town? Venture out of your holiday home and check out everything that makes Squirrel Island a fun spot to go on holiday. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Maine State Aquarium (2.4 mi / 3.8 km)
  • Boothbay Golf Course (4.7 mi / 7.5 km)
  • Pemaquid Craft Co-op (8 mi / 12.8 km)

Exploring the natural landscape of Squirrel Island

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Squirrel Island is a great place to get out in nature. Here are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • Grimes Cove Beach (1.9 mi / 3 km)
  • Cabbage Island (2.6 mi / 4.2 km)
  • Barrett Park (2.8 mi / 4.5 km)
  • Coastal Maine Botanical Gardens (4.6 mi / 7.4 km)
  • Pemaquid Point Lighthouse Park (6.5 mi / 10.5 km)
  • Pemaquid Beach Park (7 mi / 11.3 km)

Transport options to and around Squirrel Island

Fly into Wiscasset, ME (ISS), the closest airport, located 11.4 mi (18.3 km) from the city centre.

Frequently asked questions

What is the best area to stay in Squirrel Island when booking a holiday rental?
When considering a holiday rental on Squirrel Island, Maine, the best area to stay is typically near the centre of the island, where visitors can enjoy easy access to both the picturesque waterfront and the charming community atmosphere. This central location often features a variety of properties, from quaint cottages to larger family homes, ensuring there is something to suit different preferences and budgets.One of the island's top attractions is the stunning natural beauty surrounding the area, with opportunities for scenic walks and breathtaking views of the Atlantic Ocean. Additionally, the nearby beaches are superb for sunbathing, swimming, or simply enjoying a leisurely stroll along the shore.Another highlight of Squirrel Island is its rich history and community spirit, which can be felt in the local gathering spots and events that take place throughout the summer. Staying near the heart of the island allows you to immerse yourself in this unique environment while enjoying the many amenities and attractions that Squirrel Island has to offer.
What are the top attractions in Squirrel Island?
Squirrel Island is a charming destination known for its serene atmosphere and natural beauty. One of the top attractions is the island's picturesque beaches, great for sunbathing and swimming during the warmer months. The small community is largely pedestrian, allowing visitors to enjoy leisurely walks along the scenic paths while taking in stunning ocean views.The historic Squirrel Island Library is a great point of interest, offering a quaint place to read and engage with the local community. Additionally, the island is surrounded by beautiful waters ideal for boating and fishing, making it a great spot for water enthusiasts.
Are all fees included in the Squirrel Island holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Squirrel Island holiday homes with parking?
Stayz offers a wide selection of holiday homes in Squirrel Island with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Squirrel Island holiday homes?
You can find great discounts on holiday homes in Squirrel Island on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Squirrel Island holiday home booking on Stayz?
To find Squirrel Island holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Squirrel Island?
A long-stay holiday home in Squirrel Island is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Squirrel Island holiday home?
Book your Squirrel Island holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Squirrel Island?
Prices for holiday homes in Squirrel Island vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Squirrel Island to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.