A calm lake surrounded by autumn-colored trees and a distant mountain range.

Holiday Homes in Cumberland Center

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Cumberland Center holiday homes

A compact kitchen with a dishwasher, microwave, and coffee maker on the countertop.

1. Quiet Spot in lovely Freeport neighborhood

Quiet Spot in lovely Freeport neighborhood
Freeport
The price is NZ$653
includes taxes & fees
13 Oct - 14 Oct
Quiet Spot in lovely Freeport neighborhood
A spacious living room with a sofa, ottoman, and coffee table, a dining area with chairs, and a kitchen with cabinets and appliances.

2. Luxe 5 Bed/ 3 Bath with Game Room & AC

Luxe 5 Bed/ 3 Bath with Game Room & AC
Yarmouth
10.0 out of 10, Exceptional, (4 reviews)
"What a great place to stay! The home is very clean and very quiet. Our host was very responsive to any questions we had. We would book this one over and over again."
United States
Michelle T.
The price is NZ$1,718
includes taxes & fees
13 Oct - 14 Oct
Luxe 5 Bed/ 3 Bath with Game Room & AC
A modern living room with a brown leather sofa, a rustic coffee table, and a dining area with a white table and chairs.

3. Windham Lakefront: Fire Pit and Modern Comforts

Windham Lakefront: Fire Pit and Modern Comforts
Windham
9.6 out of 10, Exceptional, (4 reviews)
"It was perfect for our girls trip to Portland. Private, surrounded by woods, cozy and clean! We even saw wild turkeys and deer in the yard."
United States
Jonny D.
The price is NZ$1,514
includes taxes & fees
28 Oct - 29 Oct
Windham Lakefront: Fire Pit and Modern Comforts
A spacious living area with a blue sofa, a coffee table, and a kitchen in the background.

4. 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, (15 reviews)
"Very nice! Would stay again and would highly recommend."
United States
Peter H.
The price is NZ$1,431
includes taxes & fees
18 Oct - 19 Oct
New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10
A dirt path in a park with autumn foliage.

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 NZ$1,072
includes taxes & fees
13 Oct - 14 Oct
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
A modern kitchen with dark cabinetry, stainless steel appliances, and a large island.

6. Gorgeous 3-bedroom house in charming Portland

Gorgeous 3-bedroom house in charming Portland
North Deering
9.0 out of 10, Wonderful, (4 reviews)
"This place was exactly as it looks in the photos. Really conveniently located with good amenities."
United States
Bridget M.
The price is NZ$1,239
includes taxes & fees
31 Oct - 1 Nov
Gorgeous 3-bedroom house in charming Portland
A hallway with a large, rustic mirror leaning against the wall, a potted plant in the foreground, and a glimpse of a bed with a yellow blanket in the background.

7. Lush Coastal Downtown Home - Beaches & Shopping

Lush Coastal Downtown Home - Beaches & Shopping
Freeport
10.0 out of 10, Exceptional, (7 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.
Lush Coastal Downtown Home - Beaches & Shopping
A window with a view of a snowy landscape and bare trees.

8. Tranquility between the Lakes & Sea

Tranquility between the Lakes & Sea
Westbrook
The price is NZ$577
includes taxes & fees
14 Oct - 15 Oct
Tranquility between the Lakes & Sea
A house with a wooden front door, a stone staircase, and a porch with a wooden railing.

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, (82 reviews)
"Very nice houseLots of roomKitchen well appointed"
United States
george f.
The price is NZ$2,095
includes taxes & fees
19 Oct - 20 Oct
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
A covered porch with a view of a lake and trees.

10. Mere Point Sunrise Views at Eastern Shore!

Mere Point Sunrise Views at Eastern Shore!
Brunswick
9.8 out of 10, Exceptional, (10 reviews)
The price is NZ$686
includes taxes & fees
13 Oct - 14 Oct
Mere Point Sunrise Views at Eastern Shore!
A room with a sliding glass door leading to an outdoor deck with Adirondack chairs and a table.

11. Three bedroom in United States of America, Freeport

Three bedroom in United States of America, Freeport
Freeport
10.0 out of 10, Exceptional, (13 reviews)
"All we could say was wow! Words cannot express the view from this house! It looked like a picture! Beautiful view, fully loaded kitchen, spacious, comfortable beds, everything was perfect. I have the worst cell service and I couldn’t get the app to work but David answered my call right away and helped us get in. I’d highly recommend this property and we can’t wait to come back!"
United States
Michael L.
The price is NZ$1,597
includes taxes & fees
8 Nov - 9 Nov
Three bedroom in United States of America, Freeport
A staircase with white railings and wooden steps leading to a dining area with a table and chairs.

12. 1200 sq ft ♦ West End Townhouse ♦ Perfect Location

1200 sq ft ♦ West End Townhouse ♦ Perfect Location
West End
8.4 out of 10, Very good, (62 reviews)
"Nice place, good location and very responsive host. I would definitely stay again when in Portland."
United States
Susan d.
The price is NZ$694
includes taxes & fees
20 Oct - 21 Oct
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
A grassy area with a picnic table and chairs, a body of water, and two trees in the background.

13. Orchid Harbor, Bailey Island 3BR

Orchid Harbor, Bailey Island 3BR
Harpswell
10.0 out of 10, Exceptional, (13 reviews)
"Lovely property, close to what we needed and wanted, host communicated promptly. Would definitely stay there again."
United States
Jane D.
The price is NZ$787
includes taxes & fees
27 Oct - 28 Oct
Orchid Harbor, Bailey Island 3BR
A storefront with the sign "OYSTERS" and a "RAW BAR" sign above the entrance.

14. Modern & Sunny House Steps from the Promenade.

Modern & Sunny House Steps from the Promenade.
Munjoy Hill
10.0 out of 10, Exceptional, (47 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is NZ$899
includes taxes & fees
1 Nov - 2 Nov
Modern & Sunny House Steps from the Promenade.
A spacious living room with large windows, a sofa, a chair, and a small table.

15. 1 Mi to Maine Street! MCM-Style Home in Brunswick

1 Mi to Maine Street! MCM-Style Home in Brunswick
Brunswick
9.6 out of 10, Exceptional, (12 reviews)
"Quiet, clean, well appointed house close to Maine St Brunswick and convenient to both Portland and points north. "
United States
Kendra G.
The price is NZ$573
includes taxes & fees
20 Oct - 21 Oct
1 Mi to Maine Street! MCM-Style Home in Brunswick
A modern kitchen with a bar area, wooden ceiling, and skylights.

16. The Barnhouse with hot tub

The Barnhouse with hot tub
New Gloucester
9.8 out of 10, Exceptional, (10 reviews)
"This was the perfect spot for my friends and I who were attending a wedding down the road! Great location, lovely property and very clear instructions from the hosts! "
United States
Jen V.
The price is NZ$631
includes taxes & fees
13 Oct - 14 Oct
The Barnhouse with hot tub
A wooden deck with outdoor seating and string lights.

17. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (74 reviews)
"The house was lovely and well kept and in a great location."
United States
Angela M.
The price is NZ$646
includes taxes & fees
14 Oct - 15 Oct
Full sized home
A lush garden with a hammock, a variety of flowers, and a lake in the background.

18. Classic New England Waterfront House Big Lawn Beautiful Sunrise

Classic New England Waterfront House Big Lawn Beautiful Sunrise
Harpswell
10.0 out of 10, Exceptional, (2 reviews)
"We had a wonderful stay! "
United States
Ashma B.
The price is NZ$3,058
includes taxes & fees
3 Nov - 4 Nov
Classic New England Waterfront House Big Lawn Beautiful Sunrise
A living room with a sofa, coffee table, and a large rug. There is a dining area with chairs and a table. The room has a mural on the wall depicting a landscape.

19. Chic 3-bedroom house in Munjoy Hill with off-street parking.

Chic 3-bedroom house in Munjoy Hill with off-street parking.
Munjoy Hill
10.0 out of 10, Exceptional, (9 reviews)
"Wow, wow, wow! My family and I all agree that this has been the best rental home we have ever stayed in. The interior design is so chic, we were truly wowed by the attention to detail in this place. The beds and pillows are also extremely comfy, we all had a great two nights of sleep here. The location of this place is phenomenal, it neighbors the Portland Observatory, many bars/cafes, and is a short walk down to the eastern promenade. We will absolutely stay here again the next time we’re in...
United States
Maris P.
The price is NZ$876
includes taxes & fees
11 Nov - 12 Nov
Chic 3-bedroom house in Munjoy Hill with off-street parking.
A building named Willard Square with a storefront and a red vehicle parked outside.

20. Willard Square Family Home

Willard Square Family Home
Willard Beach
9.8 out of 10, Exceptional, (13 reviews)
"Thoroughly enjoyed this house! "
United States
David W.
The price is NZ$1,003
includes taxes & fees
14 Oct - 15 Oct
Willard Square Family 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 Center Hotel Reviews

DoubleTree by Hilton Hotel Portland

DoubleTree by Hilton Hotel Portland

8/10 Good
"Too many people in the pool"
Aaron 1-night trip
Posted less than an hour ago
DoubleTree by Hilton Hotel Portland

Find out more about Cumberland Center

Cumberland Center Holiday Homes information

Number of reviews
342
Accommodation
782 Holiday Homes
Lowest Price
NZ$573
Highest Price
NZ$3,058