Cumberland County Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • 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

Featured Cumberland County Holiday Rentals

Living area
The Weldon Hotel

Aparthotel in Downtown Portland

4.5 star property
9.8 out of 10, Exceptional, (87)
"Loved this place and would definitely stay here next time we go back."
United States
Eleni
The price is HK$1,580
HK$2,306 total
includes taxes & fees
16 Dec - 17 Dec
The Weldon Hotel
On the beach
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

Holiday Home in Bailey Island

10.0 out of 10, Exceptional, (233)
"Tremendous stay, great property and host."
United States
Curtis G.
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
Exterior
Sebago Lake Cottage on Raymond Cape

Cabin in Raymond

10.0 out of 10, Exceptional, (48)
"We loved this cabin! A stone throw from the lake. Private and quiet. "
United States
Kathy K.
Sebago Lake Cottage on Raymond Cape
Exterior detail
Sunny Modern Oasis in Portland’s Trendy East End

Holiday Home in Munjoy Hill

10.0 out of 10, Exceptional, (62)
"Cozy, clean and quiet, within short walking distance to restaurants, coffee shops, breweries, distilleries and shopping. "
United States
Jane
Sunny Modern Oasis in Portland’s Trendy East End
TV
In-town no frills 2 bedroom apt

Apartment in West Bayside

8.6 out of 10, Excellent, (16)
"Host was very accommodating. Apartment worked well for. Description accurate. Would stay again."
United Kingdom
Martha F.
The price is HK$654
HK$1,213 total
includes taxes & fees
1 Dec - 2 Dec
In-town no frills 2 bedroom apt
Smart TV
Beautiful 1st Floor Apartment & Amazing Shower

Apartment in Parkside

9.0 out of 10, Wonderful, (26)
"My brother in law and I stayed here while my husband was hospitalized at the Maine Med and it was a lovely property. Everything was clean and organized, check in was easy and the hosts were responsive and kind. I would stay here again!"
United States
Lillian L.
The price is HK$463
HK$1,141 total
includes taxes & fees
26 Nov - 27 Nov
Beautiful 1st Floor Apartment & Amazing Shower
Property grounds
THE LILLIPAD.Off-grid A frame. Sebago lake region!

Cabin in Standish

9.8 out of 10, Exceptional, (6)
"Charming cabin. Well maintained. Loved my stay! Highly recommend."
United States
Danny B.
The price is HK$1,129
HK$1,400 total
includes taxes & fees
27 Nov - 28 Nov
THE LILLIPAD.Off-grid A frame. Sebago lake region!
1 bedroom, bed sheets
Studio Unit Walkable Everywhere

Apartment in West Bayside

5.8 out of 10, (6)
"We didn't stay there at all. Canceled reservation "
United States
Dianne
The price is HK$572
HK$1,131 total
includes taxes & fees
23 Nov - 24 Nov
Studio Unit Walkable Everywhere
Fridge, microwave, oven, stovetop
Private Entrance Residential Portland

Apartment in Deering Center

9.2 out of 10, Wonderful, (5)
"Great location for seeing the Portland Head Lighthouse. Comfortable bed."
United States
Michelle S.
Private Entrance Residential Portland
Interior
Charming Studio apartment with WiFi, AC in welcoming Portland

Apartment in Munjoy Hill

9.6 out of 10, Exceptional, (11)
"This was a great stay through and through. Excellent condition, very responsive before and during the stay, and a great location. 10/10 will recommend to anyone staying in Portland! "
United States
Kirsten
The price is HK$973
HK$1,790 total
includes taxes & fees
28 Nov - 29 Nov
Charming Studio apartment with WiFi, AC in welcoming Portland
Fridge, microwave, oven, stovetop
The Globe House on Munjoy Hill - Walk to Breweries

Holiday Home in Munjoy Hill

10.0 out of 10, Exceptional, (92)
"Beautiful house in great area."
United States
Amber W.
The Globe House on Munjoy Hill - Walk to Breweries
Exterior
Beautiful Oceanfront House- Stunning Water Views

Holiday Home in Harpswell

9.4 out of 10, Exceptional, (23)
"We loved our stay! Gorgeous view, lots of thoughtful little amenities. The home was extremely clean and the host was just lovely. "
United States
Catherine O.
Beautiful Oceanfront House- Stunning Water Views
Property grounds
WATERFRONT ON PETTENGILL POND

Cottage in WINDHAM

9.6 out of 10, Exceptional, (4)
"My kids and I loved our stay at the pond. We enjoyed kayaking and floating in the peaceful setting. "
United States
Darby F.
WATERFRONT ON PETTENGILL POND
Fridge, oven, stovetop, coffee/tea maker
Updated Long Island Maine Cottage

Cottage in Long Island

10.0 out of 10, Exceptional, (7)
"Great island house! Loved how stocked the kitchen was, we had comfortable beds and even beach chairs and cooler. We would definitely stay here again. "
United States
Serra C.
Updated Long Island Maine Cottage
Exterior
Romantic getaway for 2 PEAK fall foliage!!!

Cabin in Naples

10.0 out of 10, Exceptional, (313)
"Peaceful and relaxing it was the perfect getaway"
United States
melissa d.
Romantic getaway for 2 PEAK fall foliage!!!
Interior
Downtown Penthouse Suite - Stunning Harbor Views

Apartment in Downtown Portland

10.0 out of 10, Exceptional, (224)
"Outstanding customer service and the view from our loft was incredible. I can’t say enough about how much we enjoyed our stay and we look forward to coming back someday."
United States
Scott M.
Downtown Penthouse Suite - Stunning Harbor Views
Exterior
Charming lakefront cottage with a dock, WiFi, & washer/dryer - dogs welcome

Cabin in Windham

8.8 out of 10, Excellent, (48)
"Beautiful setting on the water and a quaint little cottage with everything we needed. It was a little rustic but very comfortable!"
United States
Katherine C.
Charming lakefront cottage with a dock, WiFi, & washer/dryer - dogs welcome
Property grounds
Charming 2-bedroom house with AC, WiFi in lovely Falmouth

Holiday Home in Falmouth

8.8 out of 10, Excellent, (6)
"We had a wonderful stay. Nice comfortable camp. We enjoyed swimming in the lake. "
United States
Darcie B.
Charming 2-bedroom house with AC, WiFi in lovely Falmouth
Outdoor dining
New Well Built Elegant Home on the Water 2 miles to Freeport, 9 to Portland!

Holiday Home in South Freeeport

9.8 out of 10, Exceptional, (197)
"Beautiful location and a charming home for a family get-together. The house was well stocked and had all the amenities needed to make the stay comfortable. The host was responsive to all our questions. We had a wonderful time and look forward to coming back to coastal Maine."
United States
Shailesh M.
New Well Built Elegant Home on the Water 2 miles to Freeport, 9 to Portland!
Fridge, microwave, oven, stovetop
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Holiday Home in East Deering

10.0 out of 10, Exceptional, (65)
"Nice stay. Good amenities. "
United States
Laura H.
The price is HK$5,429
HK$8,285 total
includes taxes & fees
1 Dec - 2 Dec
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
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

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Cumberland County Hotel Reviews

Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

10/10 Excellent
"Awesome stay. I will definitely return "
MAURICE 2-night trip
Posted 10 hours ago
Canopy by Hilton Portland Waterfront