Holiday rentals in Penobscot Bay

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Top-rated holiday rentals in Penobscot Bay

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

Superhost

Flat in Searsport

4.82 out of 5 average rating, 290 reviews

Lakefront Vacation Apartment in Searsport ME

All season private top floor apartment. Hammock, loungers, floats. Acadia/State parks close. Canoe, kayaks, hot tub/wood floating dock (seasonal use), fire pit, grill, swim, fish. Modern/Antique furnished: queen bed plus loveseat twin. Massage/lounger. 2nd queen, twin inflatables. Fully equipped kitchen. Families w/kids, business guests welcome. Wifi smart TV. Great hikes, mountain bike rentals close. Snow shoes/sled included, skiing close. Separate entrance/apt above home not full home.

24–31 Oct

$136 SGD per night
Guest favourite

Yurt in Appleton

4.96 out of 5 average rating, 221 reviews

SUMMER ROSE a Yurt for ALL Seasons

SUMMER ROSE - Overlooking the Field of Dreams pasture, and future pond, is a spacious wooden yurt with a spectacular ceiling, personal hot tub and "Hideout" a screened in sanctuary. The Appleton Retreat is situated on 120 acres of privately owned land. To the south, a short walk from Summer Rose, is the Pettengill Stream, a resource protected area where you can view wildlife or kayak; and to the north, a wooded trail leads to a secluded pond on 1,300 acres of Nature Conservancy protected land.

16–23 Feb

$220 SGD per night
Guest favourite

Guest house in Orland

4.99 out of 5 average rating, 102 reviews

Cozy cottage in Orland Village-Penobscot Bay area

Charming cottage in Orland Village, 2 minutes from Bucksport, a short walk away from the Orland River and its estuary on the Penobscot Bay. Nestled on 3.5 acres of wooded land, 300 ft behind an 18th-century colonial house. Completely self-contained with equipped kitchen. Fast 400 Mbs cable internet/WiFi. 45 minutes to Acadia National Park, 30 min. to Belfast, 20 min. to Castine. Perfect base for hiking, kayaking, sailing, or discovering the maritime past of the area. Pet friendly!

3–10 Mar

$133 SGD per night

Popular amenities for Penobscot Bay holiday rentals

Other great holiday rentals in Penobscot Bay

Guest favourite

Flat in Belfast

4.99 out of 5 average rating, 106 reviews

Harborview Escape Downtown Belfast

21–28 Mar

$217 SGD per night
Guest favourite

Home in Brooks

4.89 out of 5 average rating, 196 reviews

Cedar Swamp Farm

30 Sep – 7 Oct

$154 SGD per night
Guest favourite

Cottage in Rockport

4.94 out of 5 average rating, 162 reviews

Designer’s Coastal Retreat with Simple Luxuries

14–21 Feb

$196 SGD per night
Guest favourite

Guest house in Lincolnville

4.97 out of 5 average rating, 327 reviews

"The Lair" Guesthouse

2–9 Jun

$213 SGD per night
Guest favourite

Flat in Searsmont

4.97 out of 5 average rating, 108 reviews

Searsmont Studio

13–20 Apr

$106 SGD per night
Guest favourite

Cottage in Sedgwick

4.99 out of 5 average rating, 188 reviews

Exquisitely Modern Maine Cottage @Diagonair

6–13 Jun

$535 SGD per night
Guest favourite

Cottage in Castine

4.94 out of 5 average rating, 115 reviews

Castine rustic private coast forest Acadia WiFi

6–13 Oct

$219 SGD per night
Guest favourite

Cottage in Belfast

4.99 out of 5 average rating, 87 reviews

Spectacular Cottage on Penobscot bay in Belfast

5–12 Jun

$457 SGD per night
Guest favourite

Home in Stockton Springs

4.97 out of 5 average rating, 36 reviews

Unique, Secluded, Beach House: Rocky Point

17–24 Dec

$885 SGD per night
Guest favourite

Guest house in Searsport

5.0 out of 5 average rating, 60 reviews

Private oceanfront cottage- Steps to Penobscot Bay

26 Oct – 2 Nov

$376 SGD per night
Guest favourite

Cabin in Northport

4.96 out of 5 average rating, 48 reviews

The Birch Bark Cabin

1–8 Jun

$135 SGD per night
Guest favourite

Home in Castine

5.0 out of 5 average rating, 12 reviews

Modern Brand New Home with Sweeping Views

4–11 Sep

$542 SGD per night

Destinations to explore

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  3. Maine
  4. Penobscot Bay