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 living room with a sofa, armchair, wooden coffee table, and a potted plant.

1. Fully Updated Airy Historic Home in South Freeport

Fully Updated Airy Historic Home in South Freeport
Freeport
10.0 out of 10, Exceptional, (1 review)
"Great property well kept and close to everything we wanted to do"
United States
boodu
Fully Updated Airy Historic Home in South Freeport
A compact kitchen with a dishwasher, microwave, and coffee maker on the countertop.

2. Quiet Spot in lovely Freeport neighborhood

Quiet Spot in lovely Freeport neighborhood
Freeport
The price is AU$573
includes taxes & fees
27 Oct - 28 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.

3. 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 AU$1,526
includes taxes & fees
18 Oct - 19 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.

4. 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 AU$1,210
includes taxes & fees
28 Oct - 29 Oct
Windham Lakefront: Fire Pit and Modern Comforts
A modern kitchen with dark cabinetry, stainless steel appliances, and a large island.

5. 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.
Gorgeous 3-bedroom house in charming Portland
A dirt path in a park with autumn foliage.

6. 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 AU$914
includes taxes & fees
24 Oct - 25 Oct
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
A spacious living area with a blue sofa, a coffee table, and a kitchen in the background.

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

New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10
North Deering
9.4 out of 10, Exceptional, (16 reviews)
"The house was perfect for our week in Portland. New, great features in the home, lovely backyard and close to everything Portland"
United States
Patrick J.
The price is AU$1,149
includes taxes & fees
18 Oct - 19 Oct
New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10
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 AU$471
includes taxes & fees
18 Oct - 19 Oct
Tranquility between the Lakes & Sea
A room with a sliding glass door leading to an outdoor deck with Adirondack chairs and a table.

9. 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 AU$1,243
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.

10. 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, (63 reviews)
"Nice place, good location and very responsive host. I would definitely stay again when in Portland."
United States
Susan d.
The price is AU$538
includes taxes & fees
3 Nov - 4 Nov
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
A house with a wooden front door, a stone staircase, and a porch with a wooden railing.

11. 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)
"Absolutely perfect rental!Great location with an amazing view!"
United States
Mike G.
The price is AU$1,576
includes taxes & fees
18 Oct - 19 Oct
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
A storefront with the sign "OYSTERS" and a "RAW BAR" sign above the entrance.

12. Modern & Sunny House Steps from the Promenade.

Modern & Sunny House Steps from the Promenade.
Munjoy Hill
10.0 out of 10, Exceptional, (48 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is AU$707
includes taxes & fees
19 Oct - 20 Oct
Modern & Sunny House Steps from the Promenade.
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 AU$608
includes taxes & fees
27 Oct - 28 Oct
Orchid Harbor, Bailey Island 3BR
A spacious living room with large windows, a sofa, a chair, and a small table.

14. 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 AU$469
includes taxes & fees
1 Nov - 2 Nov
1 Mi to Maine Street! MCM-Style Home in Brunswick
A modern kitchen with a bar area, wooden ceiling, and skylights.

15. 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 AU$501
includes taxes & fees
21 Oct - 22 Oct
The Barnhouse with hot tub
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.

16. 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.
Chic 3-bedroom house in Munjoy Hill with off-street parking.
A kitchen with a wooden island, black bar stools, a hanging light fixture, and a framed botanical print on the wall.

17. Spacious 4-bedroom house located in the heart of Portland, ME.

Spacious 4-bedroom house located in the heart of Portland, ME.
Munjoy Hill
10.0 out of 10, Exceptional, (22 reviews)
"Great space for our needs: three generations for a graduation weekend!"
United States
Matt H.
The price is AU$1,276
includes taxes & fees
20 Oct - 21 Oct
Spacious 4-bedroom house located in the heart of Portland, ME.
A modern kitchen with a large island, dark cabinetry, and a view of a lake.

18. The Harpswell House-1.6 Acres Waterfront, SunRise, Big Yards, Classic & Luxury

The Harpswell House-1.6 Acres Waterfront, SunRise, Big Yards, Classic & Luxury
Harpswell
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful property, well equipped, lots of amenities, plenty of space for our large group."
United States
Edwin M.
The price is AU$3,133
includes taxes & fees
19 Oct - 20 Oct
The Harpswell House-1.6 Acres Waterfront, SunRise, Big Yards, Classic & Luxury
A beach with a dock, a boat, and signs indicating a private dock and no fishing from the dock.

19. Cozy Family Home w/ Beach Access

Cozy Family Home w/ Beach Access
Raymond
The price is AU$654
includes taxes & fees
19 Oct - 20 Oct
Cozy Family Home w/ Beach Access
A modern living room with a teal sofa, two glasses of white wine, a tray of food, and a decorative candle on a wooden table.

20. Sleeps 16+ | W/D | Parking | 15 mins to Old Port

Sleeps 16+ | W/D | Parking | 15 mins to Old Port
Westbrook
10.0 out of 10, Exceptional, (1 review)
"This place was excellent, very clean, and the check-in/checkout process was very easy. The unit is broken into 3 distinct apartments with the upstairs being a one bedroom suite. However, all of the units are accessible to each other through stairs so it's convenient for staying connected while also having some separate space."
United States
damean s.
The price is AU$1,442
includes taxes & fees
25 Oct - 26 Oct
Sleeps 16+ | W/D | Parking | 15 mins 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.
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Top Cumberland Center Hotel Reviews

Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

10/10 Excellent
"The breakfast is great and the staffs are very friendly!"
Jian 2-night trip
Posted 6 hours ago
Holiday Inn Portland-By the Bay by IHG

Find out more about Cumberland Center

Cumberland Center Holiday Homes information

Number of reviews
265
Accommodation
786 Holiday Homes
Lowest Price
AU$469
Highest Price
AU$3,133