Vacation rentals in Dingley Island

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Top-rated vacation rentals in Dingley Island

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Guesthouse in South Bristol

4.98 out of 5 average rating, 342 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)

Jan 19 – 26

G$32,369 GYD per night
Guest favorite

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.

Oct 23 – 30

G$33,673 GYD per night
Guest favorite

Yurt in Chebeague Island

4.97 out of 5 average rating, 101 reviews

Yurt on Chebeague Island

Imagine staying in a yurt in the woods of Chebeague Island, nestled peacefully in a private clearing in the woods. Cozy heater for spring, fan in the summer. This yurt is “glampy” inside with leather chairs, pine log bed. The Island Yurt has a rusticator kitchen with all of the basics for cooking, small fridge, stovetop, sink. Wicked good water. Seasonal restaurants. Fire pit. Check ferry options on Casco Bay Lines or Chebeague Transportation. Host will provide transport to/from ferry to yurt.

Nov 22 – 29

G$26,056 GYD per night

Popular amenities for Dingley Island vacation rentals

Other great vacation rentals in Dingley Island

Guest favorite

Cabin in Bremen

4.95 out of 5 average rating, 173 reviews

Ocean Front Cottage: Little Heaven

Sep 25 – Oct 2

G$33,196 GYD per night
Guest favorite

Cottage in Boothbay Harbor

4.98 out of 5 average rating, 324 reviews

The Cottage at the McCobb House

Jan 24 – 31

G$34,418 GYD per night
Guest favorite

Cabin in Freedom

4.9 out of 5 average rating, 288 reviews

Cozy Lakefront Cabin in Freedom, ME

Dec 4 – 11

G$17,199 GYD per night
Guest favorite

Apartment in Boothbay Harbor

4.95 out of 5 average rating, 333 reviews

Deckhouse with Footbridge Views!

Apr 14 – 21

G$34,186 GYD per night
Guest favorite

Guesthouse in Bath

5.0 out of 5 average rating, 110 reviews

Waterfront Sunrise Cove Cottage

May 12 – 19

G$32,203 GYD per night
Guest favorite

Guesthouse in West Bath

5.0 out of 5 average rating, 15 reviews

Spruce Ledge Boathouse

Oct 25 – Nov 1

G$40,113 GYD per night
Guest favorite

Cottage in Phippsburg

5.0 out of 5 average rating, 42 reviews

Water's Edge Cottage in Phippsburg, Maine

May 20 – 27

G$68,331 GYD per night
Guest favorite

Guesthouse in Brunswick

4.94 out of 5 average rating, 87 reviews

Modern Brunswick Cottage near Bowdoin & Downtown

Dec 24 – 31

G$18,602 GYD per night
Guest favorite

Tiny home in Georgetown

5.0 out of 5 average rating, 54 reviews

Studio Cabin on Pond+Near Beach+Porch+AC+FirePit

Nov 7 – 14

G$32,109 GYD per night
Guest favorite

Guesthouse in Freeport

5.0 out of 5 average rating, 23 reviews

Mast Landing Cottage

Feb 18 – 25

G$27,044 GYD per night
Guest favorite

Cottage in Harpswell

4.98 out of 5 average rating, 47 reviews

Ocean front cottage , great water views

Jun 2 – 9

G$80,598 GYD per night
Guest favorite

Cottage in Georgetown

4.98 out of 5 average rating, 98 reviews

Cottage on Todd Bay

Oct 21 – 28

G$33,988 GYD per night

Destinations to explore

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  2. United States
  3. Maine
  4. Cumberland County
  5. Harpswell
  6. Dingley Island