Chebeague Island Vacation Rentals

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Check prices for these dates

Tonight
Apr 29 - Apr 30
Tomorrow
Apr 30 - May 1
This weekend
May 2 - May 4
Next weekend
May 9 - May 11

Vacation Rentals in Chebeague Island

The Weldon Hotel
Deluxe Suite, 2 Bedrooms | Private kitchen

The Weldon Hotel

4.0 star property
9.8 out of 10, Exceptional, (56)
"A great place to stay if you’re in town for several days. Felt like my own apt and loved the extra living space to chill after a busy week of work travels. "
The price is CA $270
CA $398 total
includes taxes & fees
May 11 - May 12
The Weldon Hotel
Gorgeous ocean-front home with stunning beach views
On the beach

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
On the beach

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 CA $207
CA $416 total
includes taxes & fees
Apr 30 - May 1
Oceanfront Condo! Spectacular Views From Private Large Balcony
Large 2BD cottage 10 min to Pier & Beach Pets ok
Exterior

Large 2BD cottage 10 min to Pier & Beach Pets ok

9.4 out of 10, Exceptional, (27)
"This property was a great place for an off-season vacation. The home was exactly as described, very clean and extremely comfortable. It is located in a quiet residential neighborhood within easy walking distance to the beach, stores and amenities. The property owner/manager was responsive when we ran into an issue and resolved it in a timely manner. I will absolutely keep this as an option for future vacations and weekends at Old Orchard Beach!"
The price is CA $221
CA $400 total
includes taxes & fees
May 1 - May 2
Large 2BD cottage 10 min to Pier & Beach Pets ok
Beach House ∆ Prime Location ∆ Steps to the Ocean
3 bedrooms, desk, iron/ironing board, travel crib

Beach House ∆ Prime Location ∆ Steps to the Ocean

10.0 out of 10, Exceptional, (40)
"Great place.... Very clean and everything you will need to stay. It was three levels and it had supplies needed for the beach (Beach wagon, chairs, towel, sand toys...). We stayed off season so most of the houses were vacant. We would definately come back again. I did send two messages to the owner, but did not get a response. "
The price is CA $208
CA $689 total
includes taxes & fees
May 5 - May 6
Beach House ∆ Prime Location ∆ Steps to the Ocean
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
Interior

Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator

9.8 out of 10, Exceptional, (202)
"I went to Wendy’s condo as a weekend getaway and I loved every minute of it! The view was amazing, the condo was clean and lovely, and the location was perfect! Wendy was really generous with letting me check in early and out late since her cleaners were not going to be there until later and she communicated well. I would 100% stay here again! "
The price is CA $311
CA $553 total
includes taxes & fees
May 4 - May 5
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
Dog-friendly cottage with deck & porch - walk to the beach, pier & town
Beach nearby

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
Studio Apartment near downtown Walkable!
1 bedroom, WiFi, bed sheets

Studio Apartment near downtown Walkable!

6.0 out of 10, (1)
"The listing said "Studio Apartment," but it is really just a bedroom with a bath. A mini-fridge, coffeemaker and microwave oven do not make this a "Studio" in the sense that I understand that word (i.e., a one-room apartment with kitchen and bath). When I went back and looked at the photos in the listing, that should have been obvious to me, but I got hung up on the word "Studio."That said, it was a comfortable room, although the bathroom was stingy on towels (no face cloths, only one hand...
The price is CA $131
CA $230 total
includes taxes & fees
May 1 - May 2
Studio Apartment near downtown Walkable!
100 feet from the ocean 3 bedroom cottage 420 friendly
Interior

100 feet from the ocean 3 bedroom cottage 420 friendly

8.6 out of 10, Excellent, (16)
"Owner should get new cleaners. House smelled like dog urine. Bathroom smelled like human urine. Had to clean floors and bathroom…lots of dirt…not sure the last time floors were I’m mopped. Dog hair on sheets. Beds were not comfortable so be prepared. Parking is a challenge. One paid parking spot in front ($36/day). Can park super close to house for 2nd spot. Owner not very responsive. Had to constantly message for arrival info and didn’t get it until 10 mins after checkin time. No instructions...
100 feet from the ocean 3 bedroom cottage 420 friendly
Rent a room in the gorgeous Holt House
Exterior

Rent a room in the gorgeous Holt House

8.0 out of 10, Very good, (24)
"This was a perfect place, close to everything in Portland! "
Rent a room in the gorgeous Holt House
Come enjoy 7 miles of beaches in sunny OOB in this 2 bedroom condo.
Beach nearby, beach towels

Come enjoy 7 miles of beaches in sunny OOB in this 2 bedroom condo.

8.2 out of 10, Very good, (34)
"I enjoyed my stay in this quaint little condo. Great location, close to the beach and a short walk to the pier. The rooms were clean and had white colored walls with grey wood floors that brightened up the space. The window air conditioner looked new and worked great! Plenty of washcloths, bath and beach towels, shampoo, conditioner and soap were provided. There was also a well stocked kitchenette. Yes, it is an older building that could use more updating, but it was fine for what I was there...
The price is CA $275
CA $516 total
includes taxes & fees
May 18 - May 19
Come enjoy 7 miles of beaches in sunny OOB in this 2 bedroom condo.
Come enjoy 7 miles of beaches in Sunny OOB in this 2 bedroom condo.
Beach nearby, beach towels

Come enjoy 7 miles of beaches in Sunny OOB in this 2 bedroom condo.

8.2 out of 10, Very good, (35)
"A cozy accommodation. Big enough for a small family that wants to spend days on the beach. Small enough for quick cleanup. My family and I enjoyed our stay."
The price is CA $173
CA $384 total
includes taxes & fees
Apr 30 - May 1
Come enjoy 7 miles of beaches in Sunny OOB in this 2 bedroom condo.
1 room luxury ocean front studio cottage
Miscellaneous

1 room luxury ocean front studio cottage

9.6 out of 10, Exceptional, (149)
"Very clean, amazinv views, perfect weekend!!!! "
1 room luxury ocean front studio cottage
Seaside Studio | Accommodates 4| Parking Available
Beach nearby

Seaside Studio | Accommodates 4| Parking Available

2.0 star property
10.0 out of 10, Exceptional, (1)
"We had a wonderful stay. The unit was immaculate and comfortable. The beach was steps away. Definitely recommend a stay!"
Seaside Studio | Accommodates 4| Parking Available
Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !
Terrace/patio

Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !

10.0 out of 10, Exceptional, (31)
"The view is beautiful and has everything you need "
Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !
68 East Grand Ave
Luxury Condo | Private kitchen

68 East Grand Ave

3.0 star property
8.8 out of 10, Excellent, (3)
"Overall good. Was told we could not stand in the Parking lot, and checkout instructions were vague. But a fabulous location- everything in walking distance! And very clean!"
68 East Grand Ave
Rent a room in the gorgeous Holt House
Exterior

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
Cozy, Elegant and Bright 2 bed in the East End
Fridge, microwave, oven, stovetop

Cozy, Elegant and Bright 2 bed in the East End

9.8 out of 10, Exceptional, (36)
"Very clean. Nice walk along bikepath to downtown. Will look to stay here again. Loved the neighborhood and parking was easy. Kitchen had everything we needed to cook. "
The price is CA $277
CA $507 total
includes taxes & fees
May 1 - May 2
Cozy, Elegant and Bright 2 bed in the East End
Soothing Oceanfront Haven with P
Beach nearby

Soothing Oceanfront Haven with P

2.0 star property
10.0 out of 10, Exceptional, (3)
"This was our first time to New England (my aunt & I), and we stayed for a couple nights here to experience the beach life in southern Maine. This was such a cute beach town, lots of quaint beach shops, great restaurants (including Johnny Schuck’s which totally changed my mind on lobster - if you stay here you have to get their lobster roll!), and of course the beach. It’s literally a two minute walk to the beach, and they have 2 beach towels included. If you want to do more beach activities...
Soothing Oceanfront Haven with P
Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!
Smart TV, video games, table tennis, books

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!
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 types of properties in Chebeague Island you may be interested in

The Westin Portland Harborview
View from property

The Westin Portland Harborview

4.0 star property
8.8 out of 10, Excellent, (1001)
"Lovely hotel for those who wish to be removed from the hustle of the Old Port. Friendly, clean, new and upscale facility. This area of Portland is a bit gritty--not at all dangerous Bar at the top of the building is very good with wonderful views."
The price is CA $187
CA $210 total
includes taxes & fees
May 26 - May 27
The Westin Portland Harborview
Portland Harbor Hotel
Honeymoon Suite, 1 King Bed

Portland Harbor Hotel

4.0 star property
9.2 out of 10, Wonderful, (1480)
"Clean, live the vibe"
The price is CA $234
CA $312 total
includes taxes & fees
May 4 - May 5
Portland Harbor Hotel
Clarion Hotel Portland
Lobby

Clarion Hotel Portland

2.5 star property
7.8 out of 10, Good, (999)
"Love the pool "
The price is CA $128
CA $142 total
includes taxes & fees
May 4 - May 5
Clarion Hotel Portland
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.

Frequently asked questions

Are there vacation rentals in Chebeague Island?

Yes, we have vacation rentals near popular attractions in Chebeague Island, or you can select a secluded option if you're looking for relaxation. Chebeague Island is known for its shopping and restaurants.

What's the top vacation rental in Chebeague Island?

Beach House ∆ Prime Location ∆ Steps to the Ocean: This vacation home rental near Chebeague Island is located on the beach and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Chebeague Island?

Expedia has 3 vacation rentals for your stay in Chebeague Island.

What can I see and do in Chebeague Island?

Explore the area and family-friendly sights such as Portland Observatory, or get out into nature at a spot like Casco Bay. Wolfe's Neck Woods State Park and Bailey Island Bridge are a couple of places you'll find in the larger area.

What are vacation rentals like in Chebeague Island?

Vacation rentals are private properties you can book for several days or more in Chebeague Island. Vacation rentals feature amenities such as WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a sanitized environment, vacation rentals can offer a sense of safety away from shared hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for a small group gathering.