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Cumberland Vacation Rentals

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Our top choices for Cumberland vacation rentals

1. 'osprey Cottage' South Freeport Home on Casco Bay!

'osprey Cottage' South Freeport Home on Casco Bay!
3.0 star property
Freeport
The price is CA $552
CA $859 total
includes taxes & fees
Sep 24 - Sep 25
'osprey Cottage' South Freeport Home on Casco Bay!

2. 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 CA $354
CA $585 total
includes taxes & fees
Sep 23 - Sep 24
Modern dome w/ full bath + spa access - 04

3. 'Osprey Cottage' South Freeport Home on Casco Bay!

'Osprey Cottage' South Freeport Home on Casco Bay!
Freeport
8.8 out of 10, Excellent, (23 reviews)
"This was an adorable cottage in a picturesque location. The cottage was clean and comfortable, right on the water. Additional friends stayed in the adjacent Heron cottage, and we joined them on the patio for a fire one evening as summer faded to autumn."
United States
John J.
The price is CA $460
CA $904 total
includes taxes & fees
Sep 24 - Sep 25
'Osprey Cottage' South Freeport Home on Casco Bay!

4. 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 CA $616
CA $880 total
includes taxes & fees
Sep 22 - Sep 23
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres

5. City Amenities, Casco Bay Sunrises and Natural Beauty

City Amenities, Casco Bay Sunrises and Natural Beauty
East Deering
9.8 out of 10, Exceptional, (132 reviews)
"Wonderful place! Owner very responsible! Would stay again! Great choice for place to stay away from home."
United States
Arlene L.
The price is CA $334
CA $591 total
includes taxes & fees
Sep 22 - Sep 23
City Amenities, Casco Bay Sunrises and Natural Beauty

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

Modern cabin w/ full bath & kitchenette - 03
Freeport
10.0 out of 10, Exceptional, (8 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 CA $248
CA $437 total
includes taxes & fees
Sep 23 - Sep 24
Modern cabin w/ full bath & kitchenette - 03

7. Lush Coastal Downtown Home - Beaches & Shopping

Lush Coastal Downtown Home - Beaches & Shopping
Freeport
10.0 out of 10, Exceptional, (6 reviews)
"Our stay was very comfortable and easy to navigate. The host was very communicative. We had everything we needed and more. It was nice to be in walking distance from downtown Freeport. Although the price was higher than we wanted, our family of four (2 teens) enjoyed having a clean, comfortable and seamless stay."
United States
Alana K.
The price is CA $420
CA $776 total
includes taxes & fees
Oct 19 - Oct 20
Lush Coastal Downtown Home - Beaches & Shopping

8. 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, (17 reviews)
"Hosts were very responsive with messages. The stay was clean and comfortable."
United States
Hana L.
The price is CA $264
CA $448 total
includes taxes & fees
Sep 20 - Sep 21
Waterfront Couples Retreat w/Porch, Private Patio, Freeport, Near LL Bean

9. 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, (80 reviews)
"Everything was very well stocked!"
United States
Sally O.
The price is CA $1,026
CA $1,617 total
includes taxes & fees
Sep 21 - Sep 22
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

10. New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10

New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10
North Deering
9.2 out of 10, Wonderful, (14 reviews)
"Very nice! Would stay again and would highly recommend."
United States
Peter H.
The price is CA $579
CA $1,137 total
includes taxes & fees
Sep 28 - Sep 29
New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10

11. Glorious getaway on Portland's Eastern Promenade.

Glorious getaway on Portland's Eastern Promenade.
Munjoy Hill
9.8 out of 10, Exceptional, (184 reviews)
"Wonderful experience with exceptional hosts!"
United States
Cynthia
The price is CA $353
CA $569 total
includes taxes & fees
Sep 20 - Sep 21
Glorious getaway on Portland's Eastern Promenade.

12. 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, (170 reviews)
"What a beautiful place to stay. Jeff and Susan made your stay a very special experience."
United States
DENESE
The price is CA $185
CA $232 total
includes taxes & fees
Sep 27 - Sep 28
Large suite/private bath/private entrance on quiet street near Thomas Bay

13. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (118 reviews)
"Really nice room and location"
United States
Victoria
The price is CA $561
CA $611 total
includes taxes & fees
Sep 22 - Sep 23
The Weldon Hotel

14. Three bedroom in United States of America, Freeport

Three bedroom in United States of America, Freeport
Freeport
9.8 out of 10, Exceptional, (10 reviews)
The price is CA $566
CA $1,315 total
includes taxes & fees
Sep 28 - Sep 29
Three bedroom in United States of America, Freeport

15. Ocean View East End Studio in a Historic Victorian

Ocean View East End Studio in a Historic Victorian
Portland
10.0 out of 10, Exceptional, (112 reviews)
"Fantastic host, fantastic place, fantastic location. 30 second walk out to a massive green lawned park overlooking the water. Easy stroll downtown. Dan was a very friendly, welcoming, and accommodating host. We had a great stay and would return again."
United States
Ryan S.
The price is CA $420
CA $645 total
includes taxes & fees
Sep 27 - Sep 28
Ocean View East End Studio in a Historic Victorian

16. Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (147 reviews)
"Owner was so accommodating!"
United States
Kiernan
The price is CA $248
CA $380 total
includes taxes & fees
Oct 20 - Oct 21
Adorable Portland getaway on the Eastern Promenade

17. Centerview cottage

Centerview cottage
Harpswell
9.6 out of 10, Exceptional, (71 reviews)
"Incredible home in a beautiful location!"
United States
Catherine G.
The price is CA $413
CA $671 total
includes taxes & fees
Sep 24 - Sep 25
Centerview cottage

18. THE RALEIGH BnB APARTMENT SELF CHECK-IN / Free Off-Street Parking

THE RALEIGH BnB APARTMENT SELF CHECK-IN / Free Off-Street Parking
Munjoy Hill
10.0 out of 10, Exceptional, (4 reviews)
"Great place, so close to everything and a clean, quiet spot to sleep."
United States
Dan K.
The price is CA $297
CA $612 total
includes taxes & fees
Sep 20 - Sep 21
THE RALEIGH BnB APARTMENT SELF CHECK-IN / Free Off-Street Parking

19. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (11 reviews)
"Truly a wonderful place with an unbeatable location. Highly recommend for a visit to Portland."
United States
Eric
The price is CA $825
CA $1,109 total
includes taxes & fees
Oct 19 - Oct 20
Evalina Hotel

20. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (68 reviews)
"The house was lovely and well kept and in a great location."
United States
Angela M.
The price is CA $283
CA $519 total
includes taxes & fees
Sep 22 - Sep 23
Full sized home
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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Top Cumberland Hotel Reviews

Find out more about Cumberland

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Cumberland. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Charming 110-year former Inn 10' from the Ocean!: This vacation home rental near Cumberland is located on the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. You can relax into your vacation with a garden and 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 Desert of Maine 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.