Deals on vacations and trips to Islesboro

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Price found within the past 48 hours. Click for updated prices.
Trade Winds on the Bay

Trade Winds on the Bay

3.5 out of 5
Price was $747, price is now $677 per person
$677
per person
Sep 28 - Oct 2
found 23 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to Rockland (RKD)
This aparthotel features an indoor pool and a gym. Guests will appreciate free perks like free self parking and WiFi in public areas. A coffee shop and laundry facilities are also provided.
Hotel Ursa

Hotel Ursa

4 out of 5
Price was $830, price is now $734 per person
$734
per person
Oct 5 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Indianapolis (IND) to Bangor (BGR)
A gym, free self parking, and concierge services are featured at this hotel. WiFi in public areas is free. A 24-hour business center, a coffee shop, and a library are also on offer.
The Craignair Inn & Restaurant

The Craignair Inn & Restaurant

3.5 out of 5
Price was $1,087, price is now $967 per person
$967
per person
Sep 28 - Oct 2
found 23 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to Rockland (RKD)
A restaurant and a bar/lounge are featured at this inn. There's no skimping on freebies - guests receive free breakfast, free WiFi, and free self parking. A terrace, a garden, and a snack bar/deli are also on offer.
Glen Mary Apartments

Glen Mary Apartments

3.5 out of 5
Price was $1,034, price is now $923 per person
$923
per person
Oct 30 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Indianapolis (IND) to Bangor (BGR)
The Lucerne Inn

The Lucerne Inn

3.5 out of 5
Lucerne-in-Maine
Price was $968, price is now $881 per person
$881
per person
Oct 5 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Indianapolis (IND) to Bangor (BGR)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Top Islesboro hotels deals

Island log home in Maine with ocean views

Island log home in Maine with ocean views

Islesboro ME
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This vacation home features a garden, laundry facilities, and barbecue grills.
Secluded And Rustic Island Cabin On The Bold And Rocky Penobscot Bay Coast...

Secluded And Rustic Island Cabin On The Bold And Rocky Penobscot Bay Coast...

Islesboro ME
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This cabin features barbecue grills.
Colonial Gables Oceanfront Village

Colonial Gables Oceanfront Village

2.5 out of 5
7 Eagle Avenue Belfast ME
Free Cancellation
Reserve now, pay when you stay
$160 nightly
The price is $174 total per night
$174 total
Sep 7 - Sep 8
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a picnic area are also on offer.
Belfast Harbor Inn

Belfast Harbor Inn

3.5 out of 5
91 Searsport Ave Belfast ME
$179 nightly
The price is $195 total per night
$195 total
Sep 2 - Sep 3
Total with taxes and fees
This hotel features an indoor pool and a gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy the seasonal outdoor pool and free perks like continental breakfast and free self parking.
Harborline Hotel

Harborline Hotel

3 out of 5
6 Park Drive Rockland ME
Free Cancellation
Reserve now, pay when you stay
$116 nightly
The price is $126 total per night
$126 total
Aug 31 - Sep 1
Total with taxes and fees
This hotel features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free continental breakfast each morning. Express check-out and luggage storage are also provided.
The Country Inn at Camden Rockport

The Country Inn at Camden Rockport

2.5 out of 5
8 Country Inn Way Rockport ME
$209 nightly
The price is $228 total per night
$228 total
Sep 1 - Sep 2
Total with taxes and fees
This hotel features an indoor pool and a gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy the hot tub and free perks like continental breakfast and free self parking.
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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.

Stay near popular Islesboro attractions

Warren Island State Park

You can take time to visit Warren Island State Park during your travels to Islesboro.
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Frequently asked questions

How much are vacation packages to Islesboro?
Adventures are calling in Islesboro, with Travelocity vacation packages starting from as low as $677. Including hotels and flights, these great deals make it really easy to see every corner of the world.
Where can I get the best vacation package deals for Islesboro?
With around 400 airlines and 1,000,000 hotels across the world, it's hard to go past Travelocity. Take advantage of our impressive range and score an incredible package deal to Islesboro. Don't you love it when traveling is that easy?
Why should I book my Islesboro vacation bundle via Travelocity?
Whether you're in search of the ultimate unplugged escape or you crave the hustle and bustle of the big smoke, booking everything with Travelocity saves you time, money and hassle. No need to comb through countless websites looking for the best deal — our Price Match Guarantee ensures you'll always get the lowest price, and our professional customer service experts are available 24/7 should you need anything at all.
Can I save money on my Islesboro car rental if I bundle it with hotels and flights?
With an Islesboro vacation package, you can combine your car, flight and hotel bookings and save loads. If you want to see the best of this fabulous city, why not make a beeline for Mount Washington State Park? This popular attraction is 120 mi from Islesboro. With your own rental car, you'll be there belong long.
What is the best time of year to go to Islesboro?
April, May and June is high season here, while November, December and January are more quiet. If your bank balance is your top consideration, try to avoid traveling during as it's typically the most expensive time. The cheapest month to explore this part of the world is .
Which airport is best for Islesboro?
For many, a stay in Islesboro means passing through Bangor Intl. Airport (BGR). This busy airport sits 35 mi north of the downtown area. You could also fly into Knox County Regional Airport (RKD) (18 mi away from central Islesboro) or Augusta State Airport (AUG) (45 mi away from central Islesboro).
What is there to do in Islesboro?
You'll find some fantastic photo opportunities at Warren Island State Park, one of the most popular attractions in Islesboro. There's a whole lot more to discover in this great city, so give yourself enough time to visit some of its lesser-known gems.
Where should I stay when visiting Islesboro?
Many travelers opt to spend their nights at the The Sea Box Island Retreat. Enjoy Ocean Views With Wooded Privacy. It's sure to be a great base for your Islesboro getaway.

Photos of local treasures

Browse Islesboro vacation photos for more inspiration

A calm lake with a dock, boats, and a forested shoreline.