Squirrel Island vacation rentals

We found 753 vacation rentals — enter your dates for availability

Discover a selection of vacation rentals in Squirrel Island that are perfect for your trip. Whether you're traveling with your kids or with friends, vacation homes have the best amenities for spending time at your vacation home, which might include a garden and pool. You'll be able to choose a rental that has what everyone needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Squirrel Island

Showing deals for:Sep 11 - Sep 18

Image gallery for Rosewater Cottage - Oceanfront on Linekin Bay!

Rosewater Cottage - East Boothbay Oceanfront
10 out of 10, Exceptional, (9 reviews)
Exceptional
(9 reviews)

Rosewater Cottage - Oceanfront on Linekin Bay!

East Boothbay

6% off
Price is $544
$3,809 for 7 nights
All fees included
Rosewater Cottage - Oceanfront on Linekin Bay!

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Find out more about Squirrel Island

Why visit Squirrel Island

  • Scenic beaches: Enjoy the pristine shores and breathtaking views of the Maine coastline.
  • Outdoor activities: Engage in hiking, exploring botanical gardens, and appreciating the vibrant wildlife.
  • Charming nearby towns: Visit Boothbay Harbor for quaint shops and small beaches.
  • Relaxing atmosphere: Experience the friendly, serene vibe perfect for unwinding and connecting with nature.
  • Diverse accommodations: Choose from private homes, cozy cottages, and family-friendly rentals for your stay.

Popular types of accommodation in Squirrel Island

Discover the charm of Squirrel Island with a variety of vacation rentals to suit your needs. Whether you're looking for a private vacation home, a cozy cottage, or a comfortable apartment, we have you covered. With beach access and nearby options like the Samoset Resort and family-friendly cottages in Southport, Squirrel Island is the perfect destination for a memorable getaway. Explore your options today and find the ideal spot for your next adventure.

  • Houses: These spacious homes are the top choice for travelers seeking comfort and privacy while enjoying Squirrel Island.
  • Cottages: Quaint and charming, cottages offer a cozy retreat, perfect for a peaceful getaway.
  • Apartments: Ideal for those looking for convenience, apartments provide a home-like feel with easy access to local attractions.
  • Cabins: Rustic and inviting, cabins are a fantastic option for nature lovers wanting to immerse themselves in the outdoors.
  • Condos: Modern condos offer upscale amenities and stunning views, making them a great choice for a luxurious stay.**

Top attractions near Squirrel Island

Squirrel Island, Maine, is an ideal destination for outdoor enthusiasts and adventure seekers. With stunning beaches, picturesque islands, and beautiful botanical gardens, it offers a variety of attractions for travelers looking to immerse themselves in nature and culture. Whether you're visiting solo, with family, or friends, Squirrel Island promises a memorable vacation filled with scenic views and outdoor experiences.

  • Coastal Maine Botanical Gardens: Explore stunning landscapes filled with native plants, vibrant flowers, and serene walking paths. Perfect for a romantic stroll or a family outing, this garden offers a peaceful retreat just 5 miles from Squirrel Island.
  • Boothbay Harbor Marina: Dive into adventure at this bustling marina, where you can enjoy boating, kayaking, and exploring the beautiful coastline. Located 3 miles from Squirrel Island, it’s an ideal spot for beach lovers and outdoor enthusiasts.
  • Cabbage Island: Experience the charm of Cabbage Island, known for its picturesque beaches and outdoor activities. Just 3 miles away, it’s perfect for a day of relaxation and fun in the sun.

Things to do recommended for couples

For a romantic getaway in Squirrel Island, indulge in a fun round at Dolphin Mini Golf, just 7 miles away, or embark on an adventurous paddle with Paddleworks, located 18 miles from the island. Both experiences promise memorable moments together in a beautiful setting.

Things to do recommended for families

Your family will have a delightful time exploring Pemaquid Point Lighthouse Park and Pemaquid Beach Park, both offering relaxing vibes just 7 miles from Squirrel Island. Fort Point, located 6 miles away, is another great spot for outdoor fun and family bonding.

Things to do recommended for groups

Groups visiting Squirrel Island can enjoy a delightful evening at the Carousel Music Theater, just 4 miles away, or hit the greens at Boothbay Golf Course, 5 miles away. Don’t miss the vibrant Boothbay Farmers' Market, also 5 miles away, for a taste of local culture and community.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Squirrel Island

If you're traveling with a group, family, pets, or planning an extended stay, it's important to prioritize your search. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Squirrel Island with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Squirrel Island with young kids: Traveling with little ones can be quite a task. It's essential to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Squirrel Island: For many families, a trip wouldn't be the same without their furry companions. If that resonates with you, take a look at Vrbo listings that welcome pets. Most of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone, including your pet, feels comfortable and at home.
  • Planning for a long term stay visiting Squirrel Island: If you're in search of vacation rentals that offer great deals for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to your search criteria as well.

Where to stay near Squirrel Island

Experience the charm of Squirrel Island, Maine, a serene getaway perfect for outdoor enthusiasts and scenic explorers. Discover the vibrant squirrel population and breathtaking views of the Maine coastline. Venture to nearby Boothbay Harbor, where quaint shops and small beaches await. Enjoy the friendly atmosphere and romantic settings that make this coastal gem an ideal destination for relaxation and adventure alike.

  • Boothbay Harbor: Located a mere 3 miles from Squirrel Island, Boothbay Harbor is a vibrant coastal town that offers a thrilling blend of outdoor adventure and stunning scenery. Visitors can embark on hiking trails that wind through lush landscapes or enjoy recreational areas perfect for picnics and relaxation. Golf enthusiasts will find excellent courses nearby. Notable attractions include beautiful beaches and the nearby national state park, which provides ample opportunities for wildlife observation and exploration. With its charming waterfront and bustling atmosphere, Boothbay Harbor is a must-visit for those seeking both adventure and relaxation.
  • Boothbay: Just 5 miles away from Squirrel Island, Boothbay is another picturesque city that captivates visitors with its natural beauty and outdoor activities. The area is known for its scenic hiking trails and recreational spots, making it ideal for adventurers and nature lovers alike. Boothbay boasts proximity to a national state park and a tranquil lake, perfect for fishing and kayaking. As you explore this charming city, you'll be surrounded by stunning landscapes and opportunities for outdoor fun, ensuring a memorable experience for all who visit.
  • Georgetown: Situated 6 miles from Squirrel Island, Georgetown is a delightful coastal town that emphasizes outdoor activities and scenic beach experiences. Whether you're looking to relax on family-friendly beaches or explore the natural beauty of local lakes, Georgetown has something for everyone. The recreational areas offer a range of activities, and visitors can also enjoy educational experiences in the area. With its captivating beaches and picturesque landscapes, Georgetown is the perfect spot for those looking to unwind and soak in the charm of Maine's coast.

Best time to go to Squirrel Island

If you're planning a trip to Squirrel Island, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from July to September, while off-peak times, like January to March tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January25.2°F (-3.8°C)Light RainMostly SunnyLowSlightly Low
February26.2°F (-3.2°C)Light RainMostly CloudyLowSlightly Low
March32.9°F (0.5°C)Light RainMostly SunnyLowSlightly Low
April43.0°F (6.1°C)Light RainMostly CloudyAverageAverage
May52.9°F (11.6°C)Light RainMostly SunnyAverageAverage
June60.8°F (16.0°C)Light RainMostly SunnyAverageSlightly High
July67.8°F (19.9°C)Light RainMostly SunnyHighSlightly High
August67.5°F (19.7°C)Light RainMostly SunnyHighSlightly High
September61.3°F (16.3°C)Light RainMostly SunnyHighAverage
October51.4°F (10.8°C)Light RainMostly SunnyAverageAverage
November40.6°F (4.8°C)Light RainMostly SunnyAverageAverage
December31.8°F (-0.1°C)Light RainMostly SunnyAverageAverage

Booking with Vrbo is simple

Looking to cut costs on your next vacation? Consider being flexible with your travel dates, as this can lead to significant savings. Also, extending your stay can often result in even better deals. To discover the ideal Vrbo property that fits your budget, utilize our filters to narrow down your options by price, location, and type of rental. We're here to help you find the perfect getaway.

Vrbo Trips: Effortless planning

Vrbo's cutting-edge Trip Board offers you a dedicated area to plan new adventures, pick up right where you left off, or keep track of your travel arrangements. You can easily find the properties you've saved or booked in the sections labeled Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Book a vacation rental for your Squirrel Island getaway

Learn about the unique charm of Squirrel Island with a stay in a private vacation home. There's no shortage of things to see and do in the area.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

Do you want to find top things to see and do in the city? Venture out of your vacation home and check out everything that Squirrel Island has to offer. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city center:

  • 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 appreciate the scenery, you'll be sure to find the perfect setting for your vacation in Squirrel Island. Here are some of the area’s most stunning features, all within 30 miles (48.2 km) of the city center:

  • Cabbage Island (2.6 mi / 4.2 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)
  • Popham Beach (8.5 mi / 13.7 km)
  • Bates-Morse Mountain Conservation Area (10.9 mi / 17.5 km)

Transportation options to and around Squirrel Island

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

Frequently asked questions

How much does it cost to rent a vacation home in Squirrel Island?
Prices for vacation rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Squirrel Island to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Squirrel Island vacation house rentals?
You can find great discounts on house rentals in Squirrel Island on Vrbo, 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 find long-stay vacation rentals in Squirrel Island?
A long-stay vacation rental in Squirrel Island is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there any Squirrel Island vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Squirrel Island with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo 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.
How early should I book a Squirrel Island vacation rental?
Book your Squirrel Island vacation rental 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 Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Squirrel Island, Maine, United States of America?
In Squirrel Island, Maine, visitors can enjoy a variety of attractions that highlight the island's natural beauty and community spirit. The island is primarily residential and offers a serene environment superb for relaxation. One of the main draws is the picturesque waterfront, where guests can take in stunning views of the Atlantic Ocean and enjoy beach access for swimming, sunbathing, and picnicking.

The island's charming cottages and historic buildings reflect its rich maritime heritage, and visitors often take leisurely walks along the scenic paths that wind through the community. For those interested in local culture, the Squirrel Island Library provides a cozy spot to read or engage in community events during the summer months.

Additionally, nearby Monhegan Island, accessible by boat, offers opportunities for hiking, art galleries, and more dramatic coastal scenery, making it a great day trip for those staying on Squirrel Island.
Can I change or cancel my Squirrel Island home rental booking on Vrbo?
To find Squirrel Island vacation rentals with free cancellation, just use Vrbo'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". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers 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, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Squirrel Island vacation rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing 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 favorites, and build the perfect itinerary together.

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