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Top Holiday Rentals in Cumberland

The Weldon Hotel

4.5 star property
9.8 out of 10, Exceptional, (68)
"Absolutely beautiful place to stay. "
The price is £354
includes taxes & fees
24 Aug - 25 Aug
The Weldon Hotel

Studio Unit Walkable Everywhere

The price is £160
includes taxes & fees
4 Aug - 5 Aug
Studio Unit Walkable Everywhere

Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.

2.0 star property
10.0 out of 10, Exceptional, (1)
"The property was as described, clean, and in a quiet neighborhood. Conveniently located to many local attractions. Check in and check out process was smooth. Overall enjoyed my stay very much. "
Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.

Refurbished waterfront 1950s cabin with sauna, firepit, grill & kayaks - dogs ok

8.0 out of 10, Very good, (11)
"We had a very nice stay cabin met all our needs"
Refurbished waterfront 1950s cabin with sauna, firepit, grill & kayaks - dogs ok

Private Entrance Residential Portland

8.0 out of 10, Very good, (1)
"Great location for seeing the Portland Head Lighthouse. Comfortable bed."
The price is £135
includes taxes & fees
30 Jul - 31 Jul
Private Entrance Residential Portland

Sebago Lake Cottage on Raymond Cape

10.0 out of 10, Exceptional, (44)
"Cozy and fun cottage. All we needed for a weekend visit for our family of 4. Morning SUP and swim was wonderful. Great hosts! We would definitely stay here again."
Sebago Lake Cottage on Raymond Cape

Escape to Serenity: Your Private Maine Lakefront Awaits at Little Sebago Lookout

9.6 out of 10, Exceptional, (85)
"The setting was absolutely beautiful. Shawn was extremely responsive and went out of his away to be accommodating. Would highly recommend!"
Escape to Serenity: Your Private Maine Lakefront Awaits at Little Sebago Lookout

Charming 2-bedroom house with AC, WiFi in lovely Falmouth

10.0 out of 10, Exceptional, (2)
"We had a wonderful stay. Nice comfortable camp. We enjoyed swimming in the lake. "
Charming 2-bedroom house with AC, WiFi in lovely Falmouth

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

10.0 out of 10, Exceptional, (222)
"We enjoyed everything about our place!"
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

In-town no frills 2 bedroom apt

7.6 out of 10, Good, (5)
The price is £156
includes taxes & fees
10 Aug - 11 Aug
In-town no frills 2 bedroom apt

Waterfront Maine cottage! Next to Sebago Lake State Park!

9.4 out of 10, Exceptional, (22)
"We had a great stay! Thank you very much for a great vacation!"
Waterfront Maine cottage! Next to Sebago Lake State Park!

Adorable Portland getaway on the Eastern Promenade

9.8 out of 10, Exceptional, (106)
"Lovely place in the top floor of a multi property house. Everything you need in a cozy space. It is a walk up so pack up light. Clean, charming and comfy. Highly recommend. "
The price is £287
includes taxes & fees
12 Aug - 13 Aug
Adorable Portland getaway on the Eastern Promenade

Great Place for a Family Retreat! Sleeps 10

9.6 out of 10, Exceptional, (11)
"Nice clean property close to everything."
Great Place for a Family Retreat! Sleeps 10

The Great Escape - Picturesque Sebago Lake

9.8 out of 10, Exceptional, (50)
"Property was perfect for our stay."
The Great Escape - Picturesque Sebago Lake

Luxury on Back Cove - Three Gables

10.0 out of 10, Exceptional, (2)
"GoodLocation, very clean. Would stay again "
The price is £433
includes taxes & fees
26 Aug - 27 Aug
Luxury on Back Cove - Three Gables

Beautiful Oceanfront House- Stunning Water Views

9.8 out of 10, Exceptional, (8)
"The Host and his wife were so pleasant and accommodating. We enjoyed watching seals, fish and birds during our visit. Highly recommend."
Beautiful Oceanfront House- Stunning Water Views

Charming 110-year former Inn 10' from the Ocean!

9.8 out of 10, Exceptional, (127)
"John was great and the view was a amazing"
Charming 110-year former Inn 10' from the Ocean!

Private Rooftop Deck!/Artsy Apt/Old Port Arts Dist

10.0 out of 10, Exceptional, (47)
"This was a great property and even better host. We had a great time staying in downtown Portland. The apartment has great finishes. I will definitely plan to stay here again."
Private Rooftop Deck!/Artsy Apt/Old Port Arts Dist

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 £145
includes taxes & fees
20 Aug - 21 Aug
Studio Apartment near downtown Walkable!

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

8.4 out of 10, Very good, (53)
"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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Top Cumberland Hotel Reviews

Frequently asked questions

Are there holiday rentals in Cumberland?

Yes, there are holiday rentals close to the most popular sights in Cumberland, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Cumberland has to offer?

Cozy and Quiet Beautiful Home One Bedroom Private Bathroom in Portland Maine.: This holiday home rental outside of Cumberland is located on the beach, and offers a fireplace, air conditioning and a Smart TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave and an electric kettle.

What’s there to see and do in Cumberland?

Explore the area and family-friendly sights such as Bayside Bowl, or get out into nature at a spot like Casco Bay. Desert of Maine and University of New England are a couple of places you'll find in the wider area.

What’s a holiday rental in Cumberland like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Cumberland. Holiday rentals offer amenities like laundry facilities and kitchens so you'll have everything you need. If you're concerned about a sanitised environment, a holiday rental can provide a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for small groups.