Cumberland County Holiday Rentals

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Top Holiday Rentals Destinations in Cumberland County

The Weldon Hotel

4.0 star property
9.4 out of 10, Exceptional, (36)
"Overall, the stay was great. The lower-level suite was a bit noisy, as we were at ground level; however, I would highly recommend staying here if you are looking for full amenities and a short commute to everything in downtown Portland. "
The price is AU$250
includes taxes & fees
6 Mar - 7 Mar
The Weldon Hotel

Relax & Recharge! Tranquil Family-Owned, Sebago Lake Area, Pets free

9.8 out of 10, Exceptional, (112)
"When we arrived at the property, it was exactly as described in the listing and even a little larger than we expected. The setting was beautiful and so peaceful! I loved watching the water from my seat around the fire and listening to all of the woodland creatures going about their day. My son also loved that it was a "classic" Maine Camp.... it was just like one would imagine. We would definitely recommend and stay here again."
Relax & Recharge! Tranquil Family-Owned, Sebago Lake Area, Pets free

Adorable Portland getaway on the Eastern Promenade

9.8 out of 10, Exceptional, (93)
"Perfect location. Wonderful accommodations"
The price is AU$298
includes taxes & fees
23 Feb - 24 Feb
Adorable Portland getaway on the Eastern Promenade

Glorious getaway on Portland's Eastern Promenade.

10.0 out of 10, Exceptional, (144)
"Old friends (in age and longevity of relationships) met up in Portland for a weekend getaway. Great location. Great city. Enjoyed our time exploring the city culture and restaurants within easy reach but also spent long hours in the bright living room catching up over a pit of tea."
The price is AU$352
includes taxes & fees
26 Feb - 27 Feb
Glorious getaway on Portland's Eastern Promenade.

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

The Globe House on Munjoy Hill - Walk to Breweries

10.0 out of 10, Exceptional, (74)
"The Globe House was a wonderful Plato spend a couple of days while exploring Portland. The house itself was immaculate and well appointed, with extra touches that put it a step above: the fresh scent from a diffuser welcomed us, a complimentary bottle of wine awaited us in the refrigerator, and luxe amenities like L’Occitane moisturizer were provided. Great location with easily walkable and excellent restaurants. Our hosts left a fabulous “guide to Portland” for us, with many of their favorite...
The Globe House on Munjoy Hill - Walk to Breweries

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

10.0 out of 10, Exceptional, (212)
"We had a peaceful time at this home. It served as a home base for exploring. When my daughter left her most priced possession, her stuffed otter, the lovely hosts found it and shipped it back to us. We're so grateful for the thoughtfulness. "
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

Romantic getaway for 2 small and simple Winter's Back

10.0 out of 10, Exceptional, (291)
"A lovely conferable place"
Romantic getaway for 2 small and simple Winter's Back

Fall In Love With Portland!

9.6 out of 10, Exceptional, (110)
"We had a great time at Nick's apartment, it is spaceous and tastefully furnished. We were able to feel right at home and used the kitchen every day, the dining room had space for all of us which made for some great holiday meals together. The location is nearly unbeatable with just two blocks to the promenade by the water and a short walk to downtown. Congress Street, which is 50 yards from the front door, has a really cool vibe with bars, cafes and restaurants. Yet, you are clearly nestled in a...
The price is AU$775
includes taxes & fees
23 Feb - 24 Feb
Fall In Love With Portland!

Historic Home in the West End. Private Parking.

9.8 out of 10, Exceptional, (28)
"We had a lovely stay in this historic home. The decor is charming and original, beds are comfy and everything is clean. The neighborhood is attractive and quiet. The information from the host was helpful. It was great to have a dedicated parking space. As described, the kitchenette has no sink but otherwise is very well equipped for simple food/beverage preparation. We look forward to staying in the future."
The price is AU$376
includes taxes & fees
23 Feb - 24 Feb
Historic Home in the West End. Private Parking.

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 AU$570
includes taxes & fees
23 Feb - 24 Feb
Cozy, Elegant and Bright 2 bed in the East End

Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants

9.8 out of 10, Exceptional, (103)
"A great place for people looking to explore Portland. Clean, comfortable and with great communication by our host, we’d recommend it for any group looking for a home base in the area."
The price is AU$775
includes taxes & fees
23 Feb - 24 Feb
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants

Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary

9.8 out of 10, Exceptional, (68)
"Great house very comfortable and well appointed. Very roomy for our entire family. Nice to have en suite bathrooms with all the bedrooms. The host was very good with communication. Located on a busy road and the driveway is on a curve which made it a little challenging entering and exiting the property. "
Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary

City Amenities, Casco Bay Sunrises and Natural Beauty

9.8 out of 10, Exceptional, (99)
"Very comfortable, close to shopping and restaurants, clean, easily accessible"
The price is AU$503
includes taxes & fees
24 Feb - 25 Feb
City Amenities, Casco Bay Sunrises and Natural Beauty

Lakefront House

10.0 out of 10, Exceptional, (23)
" Thank you so much for sharing your lovely home with us. We had the perfect bachelorette weekend getaway! We would all definitely stay again! "
The price is AU$1,161
includes taxes & fees
24 Feb - 25 Feb
Lakefront House

Charming 2-bedroom steps from the Eastern Promenade

9.8 out of 10, Exceptional, (79)
"Had a great stay in this lovely home that was close to everything in the old port. Would love to stay again!"
Charming 2-bedroom steps from the Eastern Promenade

Charming West End Hideaway. Private Parking

10.0 out of 10, Exceptional, (24)
"Communication with the owner was seamless and there were no details missed. The location was perfect for going out and also great if you're looking to shop. The apartment was clean and adorable with a little private balcony. Would definitely stay again!"
The price is AU$309
includes taxes & fees
23 Feb - 24 Feb
Charming West End Hideaway. Private Parking

The Great Escape - Picturesque Sebago Lake

9.8 out of 10, Exceptional, (43)
"Great property located on an amazing lake sebago great amenities."
The Great Escape - Picturesque Sebago Lake

6 bedroom waterfront cabin -enjoy beautiful sunsets!

9.8 out of 10, Exceptional, (18)
"John was a phenomenal host and made sure we had all the necessary resources and information for an amazing getaway. His house has spectacular views and all the amenities that a person could ask for. Don't HESITATE BOOK NOW!"
6 bedroom waterfront cabin -enjoy beautiful sunsets!

Lakefront Cottage with Private Beach

9.8 out of 10, Exceptional, (27)
"We enjoyed our stay, the house was beautifully decorated, supplied and comfortable. The views were great, enjoyed watching folks ice fish. Also, had cold enough weather, the lake ice would sing. Enjoyed the area, would return and highly recommend. "
Lakefront Cottage with Private Beach
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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