Default HTG hotel image

Cumberland 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
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Cumberland vacation rentals

Exterior detail

1. Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
East Deering
10.0 out of 10, Exceptional, (76 reviews)
"Everything was very well stocked!"
United States
Sally O.
The price is SAR 4,789
SAR 6,677 total
includes taxes & fees
30 Aug - 31 Aug
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
Interior

2. The Outlet Studio, Rustic Comfort w Fireplace

The Outlet Studio, Rustic Comfort w Fireplace
Freeport
10.0 out of 10, Exceptional, (14 reviews)
"Very comfortable, clean, with a spacious bathroom and within walking distance of downtown Freeport and Bow Street Market"
United States
Deanna S.
The Outlet Studio, Rustic Comfort w Fireplace
Property grounds

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

Modern cabin w/ full bath & kitchenette - 03
Freeport
10.0 out of 10, Exceptional, (7 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 SAR 1,287
SAR 1,899 total
includes taxes & fees
6 Sep - 7 Sep
Modern cabin w/ full bath & kitchenette - 03
Beach

4. City Amenities, Casco Bay Sunrises and Natural Beauty

City Amenities, Casco Bay Sunrises and Natural Beauty
East Deering
9.8 out of 10, Exceptional, (131 reviews)
"Wonderful place! Owner very responsible! Would stay again! Great choice for place to stay away from home."
United States
Arlene L.
City Amenities, Casco Bay Sunrises and Natural Beauty
Property grounds

5. WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres

WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
Westbrook
9.6 out of 10, Exceptional, (43 reviews)
"Host was excellent, even thinking of bug spray, yoga mats, binoculars, and extra blankets. We loved our stay!"
United States
Genevieve W.
The price is SAR 1,517
SAR 2,165 total
includes taxes & fees
9 Aug - 10 Aug
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
Terrace/patio

6. Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (62 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
The price is SAR 788
SAR 1,367 total
includes taxes & fees
7 Sep - 8 Sep
Camp Forever cottage
Honeymoon Studio | Egyptian cotton sheets, premium bedding, down comforters, bed sheets

7. Fortland Island Campground

Fortland Island Campground
1.0 star property
Portland
10.0 out of 10, Exceptional, (3 reviews)
"It was very quiet and liked the experience of staying in a camp like setting."
United States
leela srinivas
The price is SAR 1,297
SAR 1,414 total
includes taxes & fees
23 Aug - 24 Aug
Fortland Island Campground
Property grounds

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

Modern dome w/ full bath + spa access - 04
Freeport
10.0 out of 10, Exceptional, (4 reviews)
"Pet friendly and the experience is just amazing. Thank you for having us! "
United States
Rene B.
The price is SAR 1,761
SAR 2,582 total
includes taxes & fees
7 Sep - 8 Sep
Modern dome w/ full bath + spa access - 04
Exterior

9. Large suite/private bath/private entrance on quiet street near Thomas Bay

Large suite/private bath/private entrance on quiet street near Thomas Bay
Brunswick
10.0 out of 10, Exceptional, (159 reviews)
"Susan and Jeff were amazing hosts! There were so kind, thoughtful and welcoming. The suite was extremely spacious, well decorated and very comfortable. We were very close to the Air Show which was the reason for our trip. They gave us great instructions for a short cut to the airfield and amazing dinner recommendations. We could not have chosen a better place to stay. We highly recommend this place!"
United States
Asha
The price is SAR 522
SAR 651 total
includes taxes & fees
11 Aug - 12 Aug
Large suite/private bath/private entrance on quiet street near Thomas Bay
Terrace/patio

10. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (60 reviews)
"Wonderful stay!"
United States
Erika T.
The price is SAR 760
SAR 1,385 total
includes taxes & fees
12 Aug - 13 Aug
Full sized home
Coffee/tea maker, fridge, microwave, oven

11. Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport

Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport
Freeport
10.0 out of 10, Exceptional, (10 reviews)
"Incredible location right in downtown Freeport, and an even better host. We will definitely be staying with Jared again."
United States
Jake P.
The price is SAR 995
SAR 2,672 total
includes taxes & fees
9 Aug - 10 Aug
Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport
Interior

12. Willard Beach–Apartment Near Portland & Parks

Willard Beach–Apartment Near Portland & Parks
Willard Beach
10.0 out of 10, Exceptional, (5 reviews)
"Excellent in every way."
United States
Robert B.
The price is SAR 773
SAR 1,505 total
includes taxes & fees
16 Aug - 17 Aug
Willard Beach–Apartment Near Portland & Parks
TV

13. Private Entrance Residential Portland

Private Entrance Residential Portland
Deering Center
8.6 out of 10, Excellent, (8 reviews)
"This was a great place to stay. Easy to get to all of our destinations. Place was clean and comfortable. Would stay here again. "
United States
Ameleah B.
The price is SAR 414
SAR 496 total
includes taxes & fees
30 Aug - 31 Aug
Private Entrance Residential Portland
Interior

14. Charming Studio apartment with WiFi, AC in welcoming Portland

Charming Studio apartment with WiFi, AC in welcoming Portland
Munjoy Hill
9.4 out of 10, Exceptional, (23 reviews)
"Great place! We would definitely return if we were in the area."
United States
Preston
The price is SAR 740
SAR 1,199 total
includes taxes & fees
31 Aug - 1 Sep
Charming Studio apartment with WiFi, AC in welcoming Portland
Deluxe Suite, 1 King Bed | Private kitchen | Coffee/tea maker, full-size fridge, microwave, oven

15. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (108 reviews)
"Really nice room and location"
United States
Victoria
The price is SAR 1,181
SAR 1,569 total
includes taxes & fees
1 Sep - 2 Sep
The Weldon Hotel
1 bedroom, iron/ironing board, WiFi (free), bed sheets

16. Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (139 reviews)
"Owner was so accommodating!"
United States
Kiernan
The price is SAR 740
SAR 1,175 total
includes taxes & fees
6 Sep - 7 Sep
Adorable Portland getaway on the Eastern Promenade
Outdoor dining

17. Peaceful & minutes from the Old Port with private parking

Peaceful & minutes from the Old Port with private parking
Knightville
9.6 out of 10, Exceptional, (10 reviews)
"Cute, convenient spot!"
United States
Kelly S.
The price is SAR 927
SAR 1,498 total
includes taxes & fees
4 Sep - 5 Sep
Peaceful & minutes from the Old Port with private parking
Exterior

18. Ocean View East End Studio in a Historic Victorian

Ocean View East End Studio in a Historic Victorian
Portland
9.8 out of 10, Exceptional, (108 reviews)
"Lovely view and accessibility to the Old Port area. Enjoyed our relaxing stay! Thanks Dan! "
United States
David E.
The price is SAR 1,126
SAR 1,752 total
includes taxes & fees
24 Aug - 25 Aug
Ocean View East End Studio in a Historic Victorian
House (2 Bedrooms) | Interior

19. 1 Mi to Maine Street! Mcm-style Home in Brunswick

1 Mi to Maine Street! Mcm-style Home in Brunswick
3.0 star property
Brunswick
The price is SAR 451
SAR 1,092 total
includes taxes & fees
25 Aug - 26 Aug
1 Mi to Maine Street! Mcm-style Home in Brunswick
Interior

20. Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
10.0 out of 10, Exceptional, (31 reviews)
"Cute property.. also really suitable for long stay as the amenities were complete and near groceries and some restaurants and cafes.. convenient!"
United States
Giana
The price is SAR 740
SAR 1,220 total
includes taxes & fees
1 Sep - 2 Sep
Sunny Spot with Private Parking.
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 Cumberland Hotel Reviews

Clarion Pointe South Portland

Clarion Pointe South Portland

10/10 Excellent
"Clean comfortable and quiet. Plenty of hot water"
Michael 1-night trip
Posted 4 hours ago
Clarion Pointe South Portland

Frequently asked questions

Are there vacation rentals in Cumberland?

Yes, there are vacation rentals in Cumberland close to Greely Center for the Arts, or you can choose a more secluded option if you want a relaxing stay.

What's the top vacation rental that Cumberland has to offer?

Spacious Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach: This vacation home rental near Cumberland is located on the beach and has a patio, a garden, and a barbecue grill 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. You and your friends and family can relax into your vacation with amenities like a selection of games.

What’s there to see and do in Cumberland?

Explore the area and family-friendly sights such as Maine Narrow Gauge Railroad, or get out into nature at a spot like Casco Bay. Greely Center for the Arts and Maine Mall are a couple of places you'll find in the larger area.

What’s a vacation rental in Cumberland like?

Vacation rentals are private properties you can book for several days or longer in Cumberland. Vacation rentals offer extras such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a clean environment, vacation rentals can offer a sense of safety away from public hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for family gatherings.