Holiday Homes in Casco Bay Islands

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Featured Holiday Homes in Casco Bay Islands

A beautiful ocean view cottage. Come enjoy the wonderful beach!
10.0 out of 10, Exceptional, (93)
"Perfect for a family and friends weekend! Lots of room for everyone to be comfortable!"
A beautiful ocean view cottage. Come enjoy the wonderful beach!
Stille Wasser, Quiet, secluded spot on Saco River with Dock (Boat lift option)
9.6 out of 10, Exceptional, (71)
"Enjoyed this peaceful home and property. "
Stille Wasser, Quiet, secluded spot on Saco River with Dock (Boat lift option)
Admiral's Quarters - Room 12
8.8 out of 10, Excellent, (5)
"We had a wonderful time at Admiral’s Quarters and wish we’d had one more night to spend in Boothbay Harbor. Our room was cozy and the two levels made it perfect for our family of four. The location was fantastic and John always had great recommendations for things to do or places to eat. "
The price is AU$737
includes taxes & fees
20 Nov - 21 Nov
Admiral's Quarters - Room 12
Quintessential Maine Beach Cottage
10.0 out of 10, Exceptional, (105)
"Great spot, the dog loved it too"
Quintessential Maine Beach Cottage
Charming 110-year former Inn 10' from the Ocean!
9.8 out of 10, Exceptional, (110)
"We loved the location of this property. It was far enough away from the hustle and bustle to truly relax and enjoy the ocean sounds and sunrises, but close enough that we could easily hop on over to shopping and restaurants. The property was well-maintained, we loved the deck, and being able to walk right out on the beach. Highly recommend!"
Charming 110-year former Inn 10' from the Ocean!
Newly renovated 3 bedroom, 2 bath bungalow, walking distance to downtown.
10.0 out of 10, Exceptional, (66)
"We have stayed at several VRBO and this one was the best. Great location and great house."
Newly renovated 3 bedroom, 2 bath bungalow, walking distance to downtown.
East Grand Ave Fabulous Cottage
9.2 out of 10, Wonderful, (131)
"The picture on VRBO leads you to believe you just go down the pathway shown to get to the beach when you are actually in a neighborhood and have to walk down the street to get to the beach. The house was very clean and both beds were very comfortable. The host was very fast to respond to my messages. Needs clean shower liner. We enjoyed our stay. "
East Grand Ave Fabulous Cottage
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
9.2 out of 10, Wonderful, (30)
"We had a great time. Nate made check in/check out very easy and the location is great. Would recommend staying here!"
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
Full sized home
9.6 out of 10, Exceptional, (22)
"Short visit but fun little cottage off the beaten path. Most comfortable beds ever and very responsive host and caretaker. Would stay here again. Loved the nearby waterfront restaurants."
The price is AU$582
includes taxes & fees
18 Nov - 19 Nov
Full sized home
Home In Boothbay - Holiday Getaway
9.4 out of 10, Exceptional, (10)
"Great trip. Home met all our needs. It needs tables by the couch and perhaps another chair in tv room. But it was comfortable and homey. "
Home In Boothbay - Holiday Getaway
The Gregory House in Southern Maine close to many beaches & popular destinations
9.6 out of 10, Exceptional, (13)
"My friends and I stayed for one night in the gorgeous Gregory House. We've stayed here before and absolutely love it! There are so many beautiful details to the house and it's great for larger groups. We love the game room although it's often hard to get us out of the kitchen. Laura has been an amazing host as always! Very responsive, down to earth, and great to work with. We'd love to stay here again."
The price is AU$1,754
includes taxes & fees
24 Nov - 25 Nov
The Gregory House in Southern Maine close to many beaches & popular destinations
The Sea Eagle - Luxury 5 BR Waterfront Home in Boothbay Harbor
10.0 out of 10, Exceptional, (4)
"I can’t say enough about the house and our wonderful hosts. They’ve created a wonderful memory for our friends and family that will last a lifetime. The house, the views, boothbay harbor and all that it has to offer. Best vacation ever!! THANK YOU SO MUCH!! Paul"
The Sea Eagle - Luxury 5 BR Waterfront Home in Boothbay Harbor
Oceanside escape 🌊 perfect family getaway!
9.8 out of 10, Exceptional, (10)
"Beautiful home! Well kept, clean and very comfortable. A little touch of history in this wonderful house and neighborhood. Great location, quick to Portland and the airport. We loved it!!!! Owner communication is a 10+++. "
Oceanside escape 🌊 perfect family getaway!
Spacious Kennebunkport Home w/ View, 2 Mi to Beach
10.0 out of 10, Exceptional, (43)
"We had a great time at this beautiful property. We were in town for the wedding of a family member and couldn’t have asked for a better place!"
Spacious Kennebunkport Home w/ View, 2 Mi to Beach
Sea-clusion by the sea! Cozy cottage within step of the beach!
9.4 out of 10, Exceptional, (30)
"Very nice little house. That being said, the house was good for us as we weren’t there much, but if you plan on spending a lot of time in the house it is small, the bathroom is made for small people. I would recommend this listing as the host is very quick to respond and very pleasant and helpful."
Sea-clusion by the sea! Cozy cottage within step of the beach!
Elegant condo - walk to Portland's best restaurants & Old Port
9.4 out of 10, Exceptional, (56)
"We really enjoyed this home and the location. The upgrades were beautiful and the restaurants nearby were amazing. When we checked out and took out our trash the outside bin had a lock on it so our only issue was not being able to access that but that wasn’t anyone’s fault. "
The price is AU$657
includes taxes & fees
18 Nov - 19 Nov
Elegant condo - walk to Portland's best restaurants & Old Port
Rent a room in the gorgeous Holt House
8.2 out of 10, Very good, (22)
"We loved staying at the Holt House. It's a truly beautiful building. It's like staying in a hotel from another era. The room was beautifully decorated with victorian decor and we loved it. It was also handy to have access to a full kitchen on the first floor where we washed some of our dishes. Overall, it was a cozy and quiet place to stay."
Rent a room in the gorgeous Holt House
Bayside House Near Portland with Water Views, Fast WiFi, & Patio - Dogs OK
8.6 out of 10, Excellent, (12)
"This is owners first year renting. It needs a complete review by electrician because there are several outlets not working. We also had trouble with the thermostats and heat. So that needs help too. The 1800 salt box portion of the home was charming to us. The addition added a great number of beds and baths. The kitchen was marginally stocked with bowls, etc so bring your own.. kitchen could have been cleaner too. So not smooth sailing but a comfy no fuss second home"
Bayside House Near Portland with Water Views, Fast WiFi, & Patio - Dogs OK
Lowell's Getaway. Kayaking, beaches, dining and AC from this water view home.
9.6 out of 10, Exceptional, (33)
"The house we stayed in was wonderful. It met all of our expectations. I highly recommend it!"
Lowell's Getaway. Kayaking, beaches, dining and AC from this water view home.
The Moonglow! A beautiful ocean view house in Biddeford!
9.8 out of 10, Exceptional, (93)
"We had a wonderful time! Beautiful location.. very comfortable accommodations!! "
The Moonglow! A beautiful ocean view house in Biddeford!
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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Other property types in Casco Bay Islands

Quintessential Maine Beach Cottage
10.0 out of 10, Exceptional, (105)
"Great spot, the dog loved it too"
Quintessential Maine Beach Cottage
Beachfront Luxury Grand Victorian Condo (Primetime View directly down the pier)
9.8 out of 10, Exceptional, (115)
"Very relaxing getaway."
Beachfront Luxury Grand Victorian Condo (Primetime View directly down the pier)
Sensational House on Sebago Lake, Raymond, ME
9.8 out of 10, Exceptional, (43)
"Great property located on an amazing lake sebago great amenities."
Sensational House on Sebago Lake, Raymond, ME
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.