Cumberland Vacation Rentals

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Check prices for these dates

In two weeks
Sep 19 - Sep 21
In one month
Oct 3 - Oct 5
In two months
Oct 31 - Nov 2
In three months
Nov 28 - Nov 30

Vacation Rentals in Cumberland

Our top choices for Cumberland vacation rentals

The Weldon Hotel
Deluxe Suite, 1 King Bed | Living area | LCD TV, Netflix, streaming services, music library

The Weldon Hotel

4.5 star property
9.8 out of 10, Exceptional, (76)
"Absolutely beautiful place to stay. "
The price is ￥56,246
￥72,337 total
includes taxes & fees
Sep 7 - Sep 8
The Weldon Hotel
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
On the beach

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

10.0 out of 10, Exceptional, (225)
"We had a wonderful stay at this cottage. Great location to explore the surrounding areas."
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.
1 bedroom, in-room safe, free WiFi, bed sheets

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.
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough
Private kitchen

Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough

2.0 star property
9.0 out of 10, Wonderful, (9)
"Host was very receptive and responsive while on the property. We had a great time. "
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough
Studio Unit Walkable Everywhere
1 bedroom, bed sheets

Studio Unit Walkable Everywhere

8.0 out of 10, Very Good, (2)
"Great, comfortable place to stay. The location is super walkable. There are several bars/restaurants very close, and other areas are close enlighten to walk to as well (I.e. Congress Street). Commercial is a bit of a walk, but if you’re like us and love to walk a new area. It’s not that far. The bed is comfortable and the place was very clean. Communication was great. We would stay here again!"
The price is ￥15,440
￥26,158 total
includes taxes & fees
Sep 2 - Sep 3
Studio Unit Walkable Everywhere
Refurbished waterfront 1950s cabin with sauna, firepit, grill & kayaks - dogs ok
Exterior

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

7.8 out of 10, Good, (13)
"We had a very nice stay cabin met all our needs"
Refurbished waterfront 1950s cabin with sauna, firepit, grill & kayaks - dogs ok
In-town no frills 2 bedroom apt
TV

In-town no frills 2 bedroom apt

8.0 out of 10, Very Good, (8)
"The frills of the neighborhood carried into the apartment. Floors and bathrooms seemed clean. Dishes and Keurig filthy - broken window a/c on floor. Broken chairs. No tlc for the property. Neighborhood beyond the stated description- would not recommend . Best to say is that rental car made it out with all windows and tires. Very disappointed "
The price is ￥19,300
￥30,660 total
includes taxes & fees
Sep 7 - Sep 8
In-town no frills 2 bedroom apt
Elegant and efficient Island home 4 miles from downtown Portland
Outdoor dining

Elegant and efficient Island home 4 miles from downtown Portland

9.0 out of 10, Wonderful, (2)
"An ideal home away from home at our most favorite place in Maine. Plenty of extra touches to make guests feel welcome and comfortable. Owner is quick to respond to any questions, and went well above-and-beyond to help us out when we experienced an unforeseen situation. I am so very grateful! I hope we can book this wonderful home again next summer. Thank you!"
Elegant and efficient Island home 4 miles from downtown Portland
Camp Forever cottage
Outdoor dining

Camp Forever cottage

9.6 out of 10, Exceptional, (52)
"Great stay. My husband and I were there for 4 days. Peaceful and quiet. Lovely views. Just perfect for the two of us. Short drive to area sites, businesses and restaurants."
The price is ￥19,719
￥40,247 total
includes taxes & fees
Sep 15 - Sep 16
Camp Forever cottage
Serenity - Stunning Sebago Lake scenery
Interior

Serenity - Stunning Sebago Lake scenery

10.0 out of 10, Exceptional, (44)
"Nice house , nice host , everything was great!"
Serenity - Stunning Sebago Lake scenery
Sebago Lake Cottage on Raymond Cape
Exterior

Sebago Lake Cottage on Raymond Cape

10.0 out of 10, Exceptional, (47)
"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."
The price is ￥18,581
￥35,289 total
includes taxes & fees
Sep 5 - Sep 6
Sebago Lake Cottage on Raymond Cape
Beautiful Oceanfront House- Stunning Water Views
Interior

Beautiful Oceanfront House- Stunning Water Views

9.4 out of 10, Exceptional, (13)
"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
Waterfront Maine cottage! Next to Sebago Lake State Park!
Marina

Waterfront Maine cottage! Next to Sebago Lake State Park!

9.4 out of 10, Exceptional, (26)
"We had a great stay! Thank you very much for a great vacation!"
Waterfront Maine cottage! Next to Sebago Lake State Park!
Private Entrance Residential Portland
Fridge, microwave, oven, stovetop

Private Entrance Residential Portland

9.0 out of 10, Wonderful, (4)
"Check in was simple. Quaint place. "
The price is ￥15,440
￥26,158 total
includes taxes & fees
Sep 2 - Sep 3
Private Entrance Residential Portland
Private Lakefront Estate with 180 Degree Views
Property grounds

Private Lakefront Estate with 180 Degree Views

10.0 out of 10, Exceptional, (5)
Private Lakefront Estate with 180 Degree Views
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
Fridge, microwave, oven, stovetop

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

10.0 out of 10, Exceptional, (61)
"Very clean, lots of room for gathering. Perfect location on a quiet street with great views of the lake. Plenty of towels, bedding, water, etc. Would come back!"
The price is ￥105,876
￥162,048 total
includes taxes & fees
Sep 15 - Sep 16
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
Spacious Historic Home | 7BR West End for Groups
Marina

Spacious Historic Home | 7BR West End for Groups

10.0 out of 10, Exceptional, (5)
"Seven of us stayed at this beautiful home in a perfect location by the Western Promenade. Everyone had a comfortable bed, bathrooms and showers were plentiful, and the kitchen was perfectly appointed. Both cars we had fit into the garage (an added luxury). The beds were very comfortable and had soft sheets and fluffy towels. We loved every minute of our stay and made great use of the family room. Can't thank our hosts enough...very easy to work with and I would certainly rent from them again...
The price is ￥103,229
￥235,890 total
includes taxes & fees
Sep 10 - Sep 11
Spacious Historic Home | 7BR West End for Groups
Updated Long Island Maine Cottage
Fridge, oven, stovetop, coffee/tea maker

Updated Long Island Maine Cottage

10.0 out of 10, Exceptional, (6)
"Great location. Comfortable living room. Well stocked kitchen. Great communication with owner."
Updated Long Island Maine Cottage
Walkable near downtown 1 Bedroom
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils

Walkable near downtown 1 Bedroom

6.0 out of 10, (1)
The price is ￥15,440
￥26,319 total
includes taxes & fees
Sep 10 - Sep 11
Walkable near downtown 1 Bedroom
State of Charm | Historic West End Haven
Property grounds

State of Charm | Historic West End Haven

9.6 out of 10, Exceptional, (4)
"Had a wonderful stay in Portland at State of Charm! Perfect stay- incredibly comfortable beds, fun to sit in the backyard, great location for walking around town. Would love to come back and stay here again. Thanks to the host for great communication and a wonderful, comfortable stay."
The price is ￥34,621
￥65,787 total
includes taxes & fees
Sep 8 - Sep 9
State of Charm | Historic West End Haven
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

Find out more about Cumberland

Find out more about Cumberland

Search for holiday rentals in Cumberland on Expedia! You can easily find your home rentals, villas, holiday apartments in Cumberland using one of the methods below:

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Look no further and take a look at our great range of rental properties in Cumberland!

Frequently asked questions

Are there vacation rentals in Cumberland?

Yes, there are vacation rentals close to well known attractions in Cumberland, or you can select a more remote option if you'd like a relaxing place to stay.

What's the top vacation rental that Cumberland has to offer?

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach: This vacation home rental near Cumberland is located on the beach and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

What’s there to see and do in Cumberland?

Explore the area and family-friendly sights such as Portland Observatory, 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 larger area.

What’s a vacation rental in Cumberland like?

Vacation rentals are private properties you can book for several days or longer in Cumberland. Vacation rentals offer extras such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a clean environment, vacation rentals can offer a sense of safety away from public hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for family gatherings.