House holiday rentals in Cumberland County
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Top-rated house rentals in Cumberland County
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for house rentals in Cumberland County
House rentals with a pool
Home in Bridgton
4.89 out of 5 average rating, 152 reviewsMoose Pond Mountain Escape
2–9 Oct
Home in Portland
4.94 out of 5 average rating, 70 reviews"Good Vibes" 4 Wonderful Seasons @ Portland Home!
13–20 Nov
Home in Gorham
4.68 out of 5 average rating, 25 reviewsLarge Private Maine Home with Pool in Gorham
3–10 Sep
Home in Mechanic Falls
5.0 out of 5 average rating, 4 reviewsLovely Home with Pool, Hot Tub & Dog Friendly
12–19 Jan
Home in Standish
4.95 out of 5 average rating, 40 reviews6BR+ Retreat on 3 Acres Near Lake w/AC +Pets OK
15–22 Apr
Home in Old Orchard Beach
5.0 out of 5 average rating, 56 reviewsOOB Oasis - 5BR private Retreat w/ Pool
16–23 Feb
Home in Portland
4.82 out of 5 average rating, 98 reviewsThere's No Place Like Home
1–8 Jun
Home in Old Orchard Beach
5.0 out of 5 average rating, 44 reviewsThe Happy Cottage
9–16 Jun
Weekly house rentals
Home in Oxford
5.0 out of 5 average rating, 180 reviewsThe Modern Lakehouse
11–18 Nov
Home in Yarmouth
4.92 out of 5 average rating, 486 reviewsBeautiful Coastal Maine Getaway
12–19 Nov
Home in Naples
4.99 out of 5 average rating, 135 reviewsKayak to the Causeway-50s cottage with modern vibe
9–16 Sep
Home in Freeport
4.96 out of 5 average rating, 100 reviewsSpacious costal home in Freeport, ME
5–12 Jun
Home in Bridgton
4.91 out of 5 average rating, 273 reviewsLake Region Comfort, Close to Everything!
20–27 Jun
Home in Harpswell
4.98 out of 5 average rating, 174 reviewsWaterfront Cottage On Basin Cove - Amazing Sunsets
10–17 Apr
Home in Portland
4.88 out of 5 average rating, 248 reviewsPerfectly Portland
5–12 May
Home in Bridgton
4.96 out of 5 average rating, 161 reviewsDreamy Mountain Home w/ Hot Tub Near Pleasant Mtn
5–12 Dec
Private house rentals
Home in Windham
4.95 out of 5 average rating, 65 reviewsWaterfront Gem walkable to Restaurants!
19–26 Mar
Home in Greene
4.84 out of 5 average rating, 32 reviewsBeautiful Maine Lakeside Cottage
24 Apr – 1 May
Home in Gray
5.0 out of 5 average rating, 18 reviewsLittle Sebago Lakefront Getaway
27 Sep – 4 Oct
Home in Gray
4.95 out of 5 average rating, 43 reviewscozy 3 bedroom ranch with deck and screen porch
7–14 Feb
Home in Harrison
4.94 out of 5 average rating, 53 reviewsLinden Tree Cottage
27 Mar – 3 Apr
Home in Waterboro
5.0 out of 5 average rating, 4 reviewsMountain View Getaway 4Season Maine
27 Aug – 3 Sep
Home in Windham
5.0 out of 5 average rating, 13 reviewsStunning, pets ok, private lake-house with dock.
12–19 Oct
Home in Harpswell
5.0 out of 5 average rating, 82 reviewsBrand new year-round oceanfront home with beach.
14–21 Nov
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