Waterfront holiday rentals in Cumberland

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Top-rated waterfront accommodation in Cumberland

Guests agree: These waterfront accommodation options are highly rated for location, cleanliness and more.

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Guest favourite

Guesthouse in South Bristol

4.98 out of 5 average rating, 345 reviews

Waterfront Guest House on the Maine Coast

Bright open four-season guest house with fantastic view of Jones Cove and the open ocean in beautiful South Bristol, Maine. The guest house offers privacy and independence. The top floor has an open space with kitchen, sleeping area with queen bed, bathroom. The ground floor has a desk, Smart TV, seating area and French doors that open onto a stone patio. Includes Kohler generator, fiber optic wifi, outdoor grill & fire pit. The water is tidal Owner lives on property (150 ft from guest house)

26 Feb – 5 Mar

$304 NZD per night

Guest favourite

Guest suite in New Gloucester

4.98 out of 5 average rating, 173 reviews

Peaceful Lakeside Suite w/Firepit and Kayaks

Open the double doors of your suite for direct access to a beautiful Maine lake. With a private entrance, the open concept apartment is in the walk-out basement of our log-cabin style home. Includes a kitchenette, private bathroom, enclosed unheated porch, large flat screen TV with DirecTV, washer & dryer. A patio with firepit is available (except when snow-covered). You may swim and use our kayaks and other boats, in season, at your own risk. Nice views. Quiet and peaceful. Enjoy star-gazing.

4–9 May

$233 NZD per night

Guest favourite

Cottage in Topsham

4.95 out of 5 average rating, 212 reviews

Cozy waterfront home on Merrymeeting Bay.

Our cozy cottage is the perfect romantic getaway or quiet retreat in any season. Located on a private rd with scenic waterfront view. Guests can enjoy sitting on the dock (May- October) or the jetty, watch the eagles and Osprey, use our kayaks, do some fishing, walking or biking. Sit by the propane fueled fireplace on a chilly night. Brunswick, home of Bowdoin College and a # of great restaurants and unique shops is just 5 mi. Travel by bus or train to/from Boston. Portland is @ 30 min away.

30 Oct – 6 Nov

$309 NZD per night

Guest favourite

Loft in West Gardiner

4.98 out of 5 average rating, 113 reviews

Cozy, Efficiency Apartment with Hot Tub

Keep it simple at this peaceful, centrally-located efficiency apartment. 15 minutes to Gardiner and Augusta, 15 minutes to I95/295. Less than one hour from Portland. Walk along the stream, listen to the loons or enjoy relaxing in the hot tub. If you want to paddle in a kayak, you can do that too! Eagles regularly soar overhead. Queen size bed, love seat and room enough for a pack and pay or twin air mattress. A/C, full kitchen, Keurig, microwave, toaster, dishes. Wifi and cable. Roomy parking.

26 Jun – 3 Jul

$238 NZD per night

Guest favourite

Guesthouse in Bath

5.0 out of 5 average rating, 112 reviews

Waterfront Sunrise Cove Cottage

Unwind and enjoy spectacular sunrises from this sunny waterfront cottage on a tidal cove in the Kennebec River! Less than 30 minutes to Popham Beach, this is the perfect home base for a midcoast Maine getaway. The cottage has a post-and-beam design, cozy furnishings, and expansive views across the field, pond, and cove. Bald eagles and osprey soar overhead, sturgeon leap in the river, and nights are full of stars. Best for 2 adults or a small family. Owners live on property with small dog.

24–31 May

$320 NZD per night

Guest favourite

Tiny home in Windham

4.98 out of 5 average rating, 132 reviews

Private riverside retreat

Private tiny house situated on the Pleasant river in Windham Maine surrounded by woods and nature! River is stocked with brook trout and lots of bass. Canoes are available for guest use to explore the river. The camp is located behind the main property ~500ft down a dirt road. 4X4 is recommended or you can park at the main house and it's a 3 minute walk. House is very comfortable with modern amenities. Running hot water, electricity, smart TV, wifi , firepit, outdoor shower, king sized bed.

28 Oct – 4 Nov

$297 NZD per night

Guest favourite

Apartment in Falmouth

4.96 out of 5 average rating, 137 reviews

Falmouth Waterfront Carriage House Apt

Waterviews! This 1 bedroom apt has a new “purple”mattress, above our detached garage in classic Maine waterfront neighborhood. Next door to the iconic Town Landing Market and Town Landing pier/beach. In beautiful Falmouth Foreside neighborhood. Walkable to Dockside Restaurant and marina, and 10 minute drive or bus to downtown Portland. 20 minute drive to Freeport shopping. We only accept well- behaved and house- trained dogs, no other pets are allowed for a fee of $75.00 per dog per stay.

17–24 Oct

$557 NZD per night

Guest favourite

Guest suite in Freeport

4.96 out of 5 average rating, 186 reviews

Waterfront Private Apartment just 5 min to LL Bean

Guest apartment with private entrances, king bed, pull out sofa, kitchenette, walk-in shower, and porch facing the water providing the perfect relaxing coastal Maine experience! Custom built home on 7.5 acres tucked away in the woods with waterfront access to Harraseeket Cove & South Freeport Harbor, great for kayaking! Located 5 minutes from LL Bean and Freeport's many shops, restaurants, bars, etc. Wolfes Neck State Park and its stunning coastal trails and forests are less than a mile away.

8–15 Oct

$727 NZD per night

Guest favourite

Cabin in Freeport

4.98 out of 5 average rating, 470 reviews

Cozy Cottage-Near Harbor & Park

Bailiwick Cottage is a cozy, private cottage that looks south down Freeport (Harraseeket) Harbor in Freeport, ME. It is a 4 season accommodation that is close to Freeport shopping, Portland eating, and the Adventure Schools of LL Bean. The cottage sits approximately 50 yards from our main house, has its own parking space and patio, and offers the ability to come and go as you wish. We have had 12 honeymoons in the cottage. Freeport Registration # STRR-2022-59

14–21 May

$309 NZD per night

Superhost

Home in Yarmouth

4.89 out of 5 average rating, 100 reviews

Eagle's Nest on 8 acres next little john preserve

Nestled on 8 acres overlooking Casco Bay, the Eagle's Nest cottage has 1 bedroom and 1 bathroom. Open plan with full-kitchen and living room including a queen-size sofa bed. Located on an island, you're only 20 minutes from downtown Portland and 10 minutes from downtown Yarmouth. Last but not least the cottage is a 5-minute walk from a 23-acre preserve that has numerous scenic viewpoints, tide pools and ledges, and picnic tables. Coastal Maine at its best!

8–15 Apr

$1,084 NZD per night

Guest favourite

Home in Freeport

4.85 out of 5 average rating, 249 reviews

Home On Pond in Woods - Guest Suite

Private ground-level apartment at 11 Fox Hill Rd, near downtown Freeport but in the woods, with access to great swimming pond and trails, with winter ice hockey, ice skating, and XC skiing at the property. Separate BR has full daylight sliding glass doors. Sleeper-sofa (or available air mattress) are in main part of semi-finished but pleasant basement. Private bathroom and entry/exit. Freeport Registration # STRR 2023-42

28 Sep – 5 Oct

$165 NZD per night

Guest favourite

Guest suite in Windham

4.92 out of 5 average rating, 151 reviews

Millers Private Studio on Highland Lake

If you're looking for a quiet, cozy getaway with private Highland Lake access this is the place for you. Private deck to enjoy your morning coffee, close to everything but in a country setting. 15 minutes from 95, Portland ME and Sebago Lake Region. Small boat launch available, Swimming & Fishing . Large back yard and a great window view of the lake. Wifi 100(mbps) for a work from home atmosphere.

1–8 May

$225 NZD per night