Search Vacation Homes in Chebeague Island

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Compare 589 Vacation Homes in Chebeague Island with updated reviews, rates, and availability.

Cute House -2 Blocks from Beach

9.4 out of 10, Exceptional, (24)
"Nice place with two bedrooms and a full kitchen. While it looks small from the outside, it’s is nicely roomy inside. "
Cute House -2 Blocks from Beach

Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!

8.2 out of 10, Very Good, (50)
"We had a large group and had more than enough beds and plenty of space to hang out. Would recommend for a big group or a family looking to spread out!"
Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!

The Globe House on Munjoy Hill - Walk to Breweries

10.0 out of 10, Exceptional, (76)
"Gorgeous and clean property. Can't wait to go again!"
The Globe House on Munjoy Hill - Walk to Breweries

Elegant Orchard Retreat: Generous Yard & Patio

2.0 star property
9.0 out of 10, Wonderful, (7)
"Booked for a weekend course, lovely spot, convenient location, and so close to everything you may need! Accommodating hosts, easy communication, and very responsive. "
Elegant Orchard Retreat: Generous Yard & Patio

Rent a room in the gorgeous Holt House

8.0 out of 10, Very Good, (14)
"Really cool room and in a great location only a short walk from restaurants and sights. "
Rent a room in the gorgeous Holt House

Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary

9.8 out of 10, Exceptional, (68)
"Great house very comfortable and well appointed. Very roomy for our entire family. Nice to have en suite bathrooms with all the bedrooms. The host was very good with communication. Located on a busy road and the driveway is on a curve which made it a little challenging entering and exiting the property. "
Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary

Oceanfront Home | Beach Access | Deck + Ping Pong

Oceanfront Home | Beach Access | Deck + Ping Pong

Spacious Country Home Freeport, Only 5 min to LL Bean!

9.8 out of 10, Exceptional, (12)
"We loved everything about this place. Beautiful, large home, plenty of room for 8 adults and 2 children. Large dining room for meals and family game time. So close to Freeport and all the shopping. Very clean, and the home has everything we needed. We can’t wait to go again!"
Spacious Country Home Freeport, Only 5 min to LL Bean!

Ultimate Pine Point Beach Family Compound-4 Units, 8 Bedrooms, Yard

The price is AED 5,693
AED 10,518 total
includes taxes & fees
8 May - 9 May
Ultimate Pine Point Beach Family Compound-4 Units, 8 Bedrooms, Yard

Dog-friendly cottage with deck & porch - walk to the beach, pier & town

8.2 out of 10, Very Good, (12)
"We enjoyed our brief stay"
Dog-friendly cottage with deck & porch - walk to the beach, pier & town

Beautiful House just a step from ocean

9.0 out of 10, Wonderful, (2)
"Lovely place for a couple and a child. Master bedroom was lovely. Water would not allow bathing but shower was ok in hall bath. The downstairs sleeping for two adults was a little difficult. Would have been nice to know upfront that the water was not potable. Nice touches with the set dining table and toiletries. View is amazing."
Beautiful House just a step from ocean

Oceanfront Cabin-Castle in Maine Woods

9.8 out of 10, Exceptional, (16)
"The pictures don’t do it justice. This place is amazing and everywhere you look there is another interesting object, stone, nook… So many books! The view, falling asleep to the sounds of the ocean was heavenly. Then you have the park that you can walk or drive too or if you’re adventurous you can simply walk the rocks right over. Best Easter ever!! "
Oceanfront Cabin-Castle in Maine Woods

Elegant condo - walk to Portland's best restaurants & Old Port

9.4 out of 10, Exceptional, (60)
"Great layout, well-appointed and super walkable to Old Port, the great restos on Washington and the Eastern Promenade. Only downside was communication with Vacasa: they always answered but didn’t necessarily address the issue, ie I struggled with the electronic door lock, was leaving for the weekend, they said the owner would come address it but when I returned 3 days later it had been left unlocked all weekend. Unreliable WiFi & I work remotely. Several times had to work from cafes.beautifully...
The price is AED 588
AED 1,550 total
includes taxes & fees
29 Apr - 30 Apr
Elegant condo - walk to Portland's best restaurants & Old Port

Prime City Living Townhouse by RedAwning

2.0 star property
9.0 out of 10, Wonderful, (2)
"It was very convenient. "
The price is AED 662
AED 1,988 total
includes taxes & fees
28 Apr - 29 Apr
Prime City Living Townhouse by RedAwning

Full sized home

9.8 out of 10, Exceptional, (26)
"Very clean and comfortable. Great care has gone into making it feel like a home well loved."
The price is AED 735
AED 1,241 total
includes taxes & fees
5 May - 6 May
Full sized home

Beautiful house on the Harpswell Peninsula over looking Casco Bay

9.8 out of 10, Exceptional, (59)
"Comfortable, peaceful. Everything we needed for mussels, steamers and lobster Nice to have working dock in front of us for lobsters"
Beautiful house on the Harpswell Peninsula over looking Casco Bay

Fun Family House w/Free WiFi and Furnished Patio - Short Walk to the Beach

7.4 out of 10, Good, (11)
"House was clean. The trash in the yard was over turned and spilling everywhere when we got there and there was a ton of it but it was picked up within 2 hours of us being there. Comfy house, cute. We couldn’t use the back deck there are holes in the deck covered by carpets. Great location overall we had a great family vacation with two families."
Fun Family House w/Free WiFi and Furnished Patio - Short Walk to the Beach

Welcome to Happy Place on Peaks Island

10.0 out of 10, Exceptional, (39)
"Lovely cottage."
Welcome to Happy Place on Peaks Island

Convenient Portland home 3 miles from Downtown

10.0 out of 10, Exceptional, (21)
"The reclining furniture was our favorite after running around all day! Very comfortable beds! Great place to stay!"
The price is AED 878
AED 2,470 total
includes taxes & fees
1 May - 2 May
Convenient Portland home 3 miles from Downtown

Huge Historic Downtown Townhome

10.0 out of 10, Exceptional, (1)
"From California, I put together a 21st birthday weekend in Portland for my daughter and five of her friends from Bates College. Tim, the manager, was communicative, helpful, and always available. The townhome is adorable, and the location is fantastic."
The price is AED 885
AED 1,605 total
includes taxes & fees
28 Apr - 29 Apr
Huge Historic Downtown Townhome
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 Chebeague Island

The Weldon Hotel

4.0 star property
9.6 out of 10, Exceptional, (54)
"Great hotel"
The price is AED 717
AED 1,057 total
includes taxes & fees
11 May - 12 May
The Weldon Hotel

Gorgeous ocean-front home with stunning beach views

9.6 out of 10, Exceptional, (104)
"This property worked well for us. Ocean view was fantastic, beds were comfy, garage was handy for our car. Good in shoulder season, would like to come back and try it in the summer."
Gorgeous ocean-front home with stunning beach views

Oceanfront Condo! Spectacular Views From Private Large Balcony

9.0 out of 10, Wonderful, (122)
"Great location! If you are looking for quiet time during the evening hours this isn’t the place for you as The Brunswick restaurant is directly below. If you like music and a great view, it’s an amazing spot! "
The price is AED 551
AED 1,117 total
includes taxes & fees
30 Apr - 1 May
Oceanfront Condo! Spectacular Views From Private Large Balcony
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.