Lodging Image

Chebeague Island Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Chebeague Island vacation rentals

A wooden house with a deck and a stone pathway leading to a grassy area.

1. Waterfront Couples Retreat w/Porch, Private Patio, Freeport, Near LL Bean

Waterfront Couples Retreat w/Porch, Private Patio, Freeport, Near LL Bean
Freeport
10.0 out of 10, Exceptional, (18 reviews)
"Hosts were very responsive with messages. The stay was clean and comfortable."
United States
Hana L.
The price is AED 789
AED 1,333 total
includes taxes & fees
20 Oct - 21 Oct
Waterfront Couples Retreat w/Porch, Private Patio, Freeport, Near LL Bean
A living room with a sofa, armchair, and glass coffee table. There are two lamps on side tables and a window with curtains.

2. Portland 1-bedroom with enclosed porch & parking

Portland 1-bedroom with enclosed porch & parking
Deering Center
8.2 out of 10, Very good, (15 reviews)
"As expected."
United States
Lance
The price is AED 328
AED 408 total
includes taxes & fees
13 Oct - 14 Oct
Portland 1-bedroom with enclosed porch & parking
A bedroom with a bed, a nightstand, a lamp, a door, and a staircase.

3. Great suburban location close to town!

Great suburban location close to town!
Deering Center
10.0 out of 10, Exceptional, (1 review)
"Small but cozy space, well kept, good value for the price and has all the amenities you could expect. Would be happy to stay here again."
United States
Peter H.
The price is AED 275
AED 356 total
includes taxes & fees
25 Oct - 26 Oct
Great suburban location close to town!
A wooden deck with outdoor seating and string lights.

4. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (72 reviews)
"The house was lovely and well kept and in a great location."
United States
Angela M.
The price is AED 744
AED 1,355 total
includes taxes & fees
14 Oct - 15 Oct
Full sized home
A dining table with chairs, a potted plant, and decorative items.

5. Willard Beach–Apartment Near Portland & Parks

Willard Beach–Apartment Near Portland & Parks
Willard Beach
10.0 out of 10, Exceptional, (9 reviews)
"Location and parking were perfect for our first visit to Portland"
United States
Linda
The price is AED 541
AED 1,175 total
includes taxes & fees
27 Oct - 28 Oct
Willard Beach–Apartment Near Portland & Parks
A covered porch with a view of a lake and trees.

6. Mere Point Sunrise Views at Eastern Shore!

Mere Point Sunrise Views at Eastern Shore!
Brunswick
9.8 out of 10, Exceptional, (10 reviews)
"Lovely location "
United States
Michelle S.
The price is AED 544
AED 1,467 total
includes taxes & fees
13 Oct - 14 Oct
Mere Point Sunrise Views at Eastern Shore!
A bedroom with a wooden bed, a nightstand, a bench, a chair, and a ceiling with a light fixture.

7. Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.4 out of 10, Very good, (21 reviews)
"We had a great stay in Portland! The place was just as described and the hosts were easy to communicate with. A good place for a couple nights within walking distance of all Portland has to offer."
United States
Lucy T.
The price is AED 289
AED 553 total
includes taxes & fees
1 Nov - 2 Nov
Studio Apartment near downtown Walkable!
A cabin with two chairs facing a fire pit, surrounded by trees.

8. Modern cabin w/ full bath & kitchenette - 03

Modern cabin w/ full bath & kitchenette - 03
Freeport
10.0 out of 10, Exceptional, (9 reviews)
"Easy check in process. More than clean, it looked brand new. Overall a great stay. Kitchen was well stocked with plates, utensils, and cookware. "
United States
Michael H.
The price is AED 1,003
AED 1,561 total
includes taxes & fees
28 Oct - 29 Oct
Modern cabin w/ full bath & kitchenette - 03
A kitchen with a wooden countertop, a black kettle, a vase with flowers, and a small wire basket.

9. Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland

Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland
Munjoy Hill
9.6 out of 10, Exceptional, (31 reviews)
"Had a wonderful stay. Very clean and great location."
United States
Aimee S.
The price is AED 459
AED 849 total
includes taxes & fees
1 Nov - 2 Nov
Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland
A street lined with buildings, one with a red door and a sign that reads "MINATO".

10. Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (153 reviews)
"Owner was so accommodating!"
United States
Kiernan
The price is AED 650
AED 1,013 total
includes taxes & fees
20 Oct - 21 Oct
Adorable Portland getaway on the Eastern Promenade
A modern house with a wooden exterior, a small garden, and a visible window.

11. Spacious and Contemporary Condo in the Heart of Portland - Close to Beach

Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
East Bayside
8.8 out of 10, Excellent, (40 reviews)
"Overall a pleasing stay."
United States
Mallory D.
The price is AED 513
AED 1,716 total
includes taxes & fees
18 Oct - 19 Oct
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
A living room with a sofa, armchairs, a coffee table, and a potted plant.

12. Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower
Parkside
9.0 out of 10, Wonderful, (32 reviews)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
The price is AED 315
AED 643 total
includes taxes & fees
4 Nov - 5 Nov
Beautiful 1st Floor Apartment & Amazing Shower
A modern kitchen with a wooden countertop, a glass coffee table, and a built-in shelf with kitchenware.

13. Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
10.0 out of 10, Exceptional, (35 reviews)
"This is a perfect location. 6 minutes from downtown Portland. Secure, Clean and Jen was a Perfect and attentive host. It is a hidden Gem!"
United States
Irish D.
The price is AED 724
AED 1,201 total
includes taxes & fees
2 Nov - 3 Nov
Sunny Spot with Private Parking.
A cozy living room with a wooden ceiling, a sofa, a table, and a sliding glass door leading to a balcony.

14. Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.2 out of 10, Wonderful, (12 reviews)
"The location and views from the cottage are quintessential coastal Maine. Small community with lobster pound and Maine Oyster Company across the street. John is a welcoming host and eager to make sure you enjoy your stay. The cottage is great for 2 people, equipped with the basics and has a great deck to enjoy the views. Planning to return next year. Great spot!"
United States
Rebecca
The price is AED 386
AED 788 total
includes taxes & fees
1 Nov - 2 Nov
Mid Coast Getaway w/ water views
A geodesic dome structure in a forest setting with a visible interior space.

15. Modern dome w/ full bath + spa access - 04

Modern dome w/ full bath + spa access - 04
Freeport
10.0 out of 10, Exceptional, (5 reviews)
"Pet friendly and the experience is just amazing. Thank you for having us! "
United States
Rene B.
The price is AED 972
AED 1,580 total
includes taxes & fees
20 Oct - 21 Oct
Modern dome w/ full bath + spa access - 04
A staircase with white railings and wooden steps leading to a dining area with a table and chairs.

16. 1200 sq ft ♦ West End Townhouse ♦ Perfect Location

1200 sq ft ♦ West End Townhouse ♦ Perfect Location
West End
8.4 out of 10, Very good, (61 reviews)
"Nice place, good location and very responsive host. I would definitely stay again when in Portland."
United States
Susan d.
The price is AED 417
AED 1,415 total
includes taxes & fees
20 Oct - 21 Oct
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
A spacious living room with large windows, a sofa, a chair, and a small table.

17. 1 Mi to Maine Street! MCM-Style Home in Brunswick

1 Mi to Maine Street! MCM-Style Home in Brunswick
Brunswick
9.6 out of 10, Exceptional, (12 reviews)
"Quiet, clean, well appointed house close to Maine St Brunswick and convenient to both Portland and points north. "
United States
Kendra G.
The price is AED 404
AED 1,217 total
includes taxes & fees
1 Nov - 2 Nov
1 Mi to Maine Street! MCM-Style Home in Brunswick
A modern kitchen with a dining area, featuring a round table, chairs, and a hanging light fixture.

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

Elegant condo - walk to Portland's best restaurants & Old Port
East Bayside
9.2 out of 10, Wonderful, (85 reviews)
"It was nice if you like being right in town. There is no view and it's a bit noisy."
United States
Nancy S.
The price is AED 617
AED 1,872 total
includes taxes & fees
12 Oct - 13 Oct
Elegant condo - walk to Portland's best restaurants & Old Port
A modern kitchen with a central island, bar stools, a dining table, and a built-in oven.

19. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (125 reviews)
"Really nice room and location"
United States
Victoria
The price is AED 737
AED 1,079 total
includes taxes & fees
2 Nov - 3 Nov
The Weldon Hotel
A room with a sliding glass door leading to an outdoor deck with Adirondack chairs and a table.

20. Three bedroom in United States of America, Freeport

Three bedroom in United States of America, Freeport
Freeport
10.0 out of 10, Exceptional, (13 reviews)
The price is AED 1,507
AED 3,477 total
includes taxes & fees
9 Nov - 10 Nov
Three bedroom in United States of America, Freeport
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chebeague Island Hotel Reviews

Quality Inn & Suites South Portland

Quality Inn & Suites South Portland

8/10 Good
"Very pleasant staff , they were knowledgeable about things in the area"
Sheila 1-night trip
Posted 13 hours ago
Quality Inn & Suites South Portland

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?

The Perfect Beach Escape: Cozy 4-Bedroom Retreat: This vacation home rental near Chebeague Island is located on the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Chebeague Island?

Expedia has 4 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 Little John Island Preserve. 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.