Orland Rentals

Close

Enter dates for more accurate prices

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more

132 Houses

(7) Excellent 

35

The Riverhouse

DownEast and Acadia Maine / Orland

Orland house

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 16 mi
  • Suitable for children age 5+

Price per night from

$139

Price per night from

$139

30

Water's Edge Rental Properties LLC

DownEast and Acadia Maine / Orland

Orland cottage

3 7 3 nights min

  • 3 bedrooms
  • sleeps 7
  • 3 nights min
  • Nearest beach 37 mi
  • Child Friendly

Price per night from

$150

Price per night from

$150

17

Charming East Orland Waterfront Home on Toddy Pond

DownEast and Acadia Maine / Orland

Orland house

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Child Friendly
  • Pet Friendly

Price per night from

$252

Responds fast!
avg. 26 minutes

Price per night from

$252

13

Charming Two Bedroom Cottage with Sunroom and Large Deck on Toddy Pond

DownEast and Acadia Maine / Orland

Orland house

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child Friendly

Price per night from

$145

Price per night from

$145

Great rentals within 20 miles that match your search

Distance approx 18.67 km from Orland

(2) Excellent 

9

Quarterdeck 2 bedroom shore front fabulous sunsets

DownEast and Acadia Maine / Trenton

Trenton cottage

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Ask about pets

Price per night from

$246

Price per night from

$246

Distance approx 8.62 km from Orland Show on Map

(13) Very Good 

20

Maine. Lovely Cottage on Penobscot Bay

DownEast and Acadia Maine / Penobscot

Penobscot cottage

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Pet Friendly
“Amazingly well equipped and idylically located.” Everything you could want in a vacation cottage except a beach. Great for a poet or a painter. Not a lot of action in the immediate neighborhood, but not far away.Quiet, well maintained and comfortable.
…see more

Price per night from

$155

Price per night from

$155

Distance approx 14.81 km from Orland

24

Gull's View

Brooksville / Harborside

Harborside house

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Child Friendly

Price per night from

$215

Price per night from

$215

Distance approx 11.5 km from Orland

16

"Eagles Nest' Mountain Retreat with 250 mile views on way to Acadia

Maine / Holden

Holden house

5 12 7 nights min

  • 5 bedrooms
  • sleeps 12
  • 7 nights min
  • Child Friendly

Price per night from

$316

Price per night from

$316

Distance approx 17.49 km from Orland

4

Beautiful Mid-Coast Maine Retreat

Mid Coast Maine / Northport

Northport house

4 8 4 nights min

  • 4 bedrooms
  • sleeps 8
  • 4 nights min
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$518

Price per night from

$518

Distance approx 14.33 km from Orland

(3) Excellent 

17

Parker House, National Register of Historic Places

DownEast and Acadia Maine / Blue Hill

Blue Hill house

3 10 4 nights min

  • 3 bedrooms
  • sleeps 10
  • 4 nights min
  • Nearest beach 3 mi
  • Child Friendly
  • Pet Friendly

Price per night from

$230

Price per night from

$230

Distance approx 16.27 km from Orland

(1) Excellent 

17

Chez Seeger, Belfast First floor apartment

Mid Coast Maine / Belfast

Belfast apartment

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$230

Price per night from

$230

Distance approx 17.11 km from Orland

36

Bayside Sunshine Cottage with Water Views Sleeps 6

Mid Coast Maine / Northport

Northport house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Child Friendly

Price per night from

$362

Price per night from

$362

Distance approx 17.17 km from Orland

13

HISTORIC BAYSIDE INN

Mid Coast Maine / Northport

Northport condo

2 5 4 nights min

  • 2 bedrooms
  • sleeps 5
  • 4 nights min
  • Beach / lakeside relaxation
  • Air conditioning

Price per night from

$288

Price per night from

$288

Distance approx 19.52 km from Orland

(6) Very Good 

Certificate of Excellence

10

Cove Cottage

DownEast and Acadia Maine / Lamoine

Lamoine house

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Child Friendly
  • Pet Friendly

Certificate of Excellence

Price per night from

$173

Price per night from

$173

Distance approx 15.55 km from Orland

34

Private beachfront oasis on Green Lake near Acadia

DownEast and Acadia Maine / Ellsworth

Ellsworth house

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$253

Price per night from

$253

Distance approx 16.54 km from Orland

22

Lakefront Cottage - Otis Street Executive Rentals

Maine / Bangor

Bangor cottage

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Child Friendly

Price per night from

$218

Price per night from

$218

Distance approx 16.19 km from Orland

24

Walk to town, shore, and parks

Mid Coast Maine / Belfast

Belfast house

3 9 4 nights min

  • 3 bedrooms
  • sleeps 9
  • 4 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Ask about pets

Price per night from

$288

Price per night from

$288

Distance approx 5.37 km from Orland Show on Map

(14) Excellent 

62

Private Sandy Beach, Sleeps 24+ large family's, Retreats and Weddings 5 star

Mid Coast Maine / Sandy Point

Sandy Point house

7 26 7 nights min

  • 7 bedrooms
  • sleeps 26
  • 7 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$690

Responds fast!
avg. 1 hour 53 minutes

Price per night from

$690

Distance approx 11.61 km from Orland

6

Luxury Sea Captain's Cottage 5 minutes from sea.

Mid Coast Maine / Searsport

Searsport house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Suitable for children age 5+

Price per night from

$238

Price per night from

$238

Distance approx 17.06 km from Orland

26

Wieland House

DownEast and Acadia Maine / Blue Hill

Blue Hill house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$445

Price per night from

$445

Distance approx 15.31 km from Orland

(4) Excellent 

17

Farm Stay Cottage @ Toddy Pond Farm

Mid Coast Maine / Belfast

Belfast house

3 7 3 nights min

  • 3 bedrooms
  • sleeps 7
  • 3 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Private garden

Price per night from

$299

Price per night from

$299

Distance approx 17.23 km from Orland

(1) Very Good 

19

Starry Nights Cottage- Bayside Village, Northport

Mid Coast Maine / Northport

Northport cottage

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly

Price per night from

$210

Responds fast!
avg. 3 hours 29 minutes

Price per night from

$210

Distance approx 17.4 km from Orland

22

Kelly Cove Cottage

Mid Coast Maine / Northport

Northport house

3 9 7 nights min

  • 3 bedrooms
  • sleeps 9
  • 7 nights min
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$215

Price per night from

$215

Distance approx 16.19 km from Orland

24

Maine Squeeze

DownEast and Acadia Maine / Surry

Surry house

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$302

Price per night from

$302

Distance approx 3.7 km from Orland Show on Map

14

Cappy's Retreat

Mid Coast Maine / Stockton Springs

Stockton Springs house

4 10 7 nights min

  • 4 bedrooms
  • sleeps 10
  • 7 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$370

Price per night from

$370

Distance approx 17.41 km from Orland

10

Waterfront Boat House

DownEast and Acadia Maine / Trenton

Trenton boathouse

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$230

Price per night from

$230

Distance approx 12.94 km from Orland

4

Sunrise Cottages - Earth Cottage

DownEast and Acadia Maine / Brooksville

Brooksville b and b

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min

Price per night from

$110

Price per night from

$110

Distance approx 15.74 km from Orland

32

Lone Gull

DownEast and Acadia Maine / Blue Hill

Blue Hill house

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Private garden

Price per night from

$237

Price per night from

$237

Distance approx 17.13 km from Orland

16

Windy Corner in Bayside, Maine

Mid Coast Maine / Northport

Northport cottage

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly

Price per night from

$374

Responds fast!
avg. 3 hours 29 minutes

Price per night from

$374

Distance approx 17.22 km from Orland

(5) Excellent 

45

The Beehive Cottage, Northport, Maine (in Bayside)

Mid Coast Maine / Northport

Northport cottage

5 12 3 nights min

  • 5 bedrooms
  • sleeps 12
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.1 mi
  • Child Friendly

Price per night from

$920

Price per night from

$920

Distance approx 16.54 km from Orland

24

Eclectic Loft - Otis Street Executive Rentals

Maine / Bangor

Bangor apartment

1 2 30 nights min

  • 1 bedroom
  • sleeps 2
  • 30 nights min
  • Child Friendly

Price per night from

$75

Price per night from

$75

Distance approx 16.54 km from Orland

24

Traditional Two Bedroom - Otis Street Executive Rentals

Maine / Bangor

Bangor apartment

2 4 30 nights min

  • 2 bedrooms
  • sleeps 4
  • 30 nights min
  • Child Friendly

Price per night from

$83

Price per night from

$83

Distance approx 16.54 km from Orland

33

Family Friendly Four Bedroom - Otis Street Executive Rentals

Maine / Bangor

Bangor apartment

4 7 30 nights min

  • 4 bedrooms
  • sleeps 7
  • 30 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$89

Price per night from

$89

Distance approx 12.43 km from Orland

(15) Excellent 

16

SWAN LAKE COTTAGE, PRIVATE BEACH, DOCK

Mid Coast Maine / Swanville

Swanville cottage

1 6 7 nights min

  • 1 bedroom
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Pet Friendly

Price per night from

$108

Responds fast!
avg. 33 minutes

Price per night from

$108

Distance approx 7.68 km from Orland

(16) Very Good 

19

Seacroft

Mid Coast Maine / Stockton Springs

Stockton Springs log cabin

1 2 7 nights min

  • 1 bedroom
  • sleeps 2
  • 7 nights min
  • Ask about pets
“clean,quiet and comfortable” very conviently located,to all that taht mid-coast Maine has to offer. Bed was comfortable and kitchen well equiped. The outside porch was a great place to relax after a busy day,with a nice view of the beautiful gardens.
…see more

Price per night from

$115

Responds fast!
avg. 35 minutes

Price per night from

$115

Distance approx 13.4 km from Orland

23

Historic Sea Captain's House Near Ocean and Parks

Mid Coast Maine / Searsport

Searsport house

5 10 5 nights min

  • 5 bedrooms
  • sleeps 10
  • 5 nights min
  • Nearest beach 25 mi
  • Child Friendly
  • Air conditioning

Price per night from

$288

Price per night from

$288

Distance approx 16.25 km from Orland

(2) Excellent 

25

Executive Waterfront Home - Near Acadia (Ellsworth) - 5BR/4Bath Sleeps 10

DownEast and Acadia Maine / Ellsworth

Ellsworth house

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Private garden

Price per night from

$591

Responds fast!
avg. 1 hour 26 minutes

Price per night from

$591

Distance approx 13.4 km from Orland

5

One Bedroom Apartment with Private Patio

Mid Coast Maine / Searsport

Searsport apartment

1 2 5 nights min

  • 1 bedroom
  • sleeps 2
  • 5 nights min
  • Air conditioning
  • Pet Friendly

Price per night from

$114

Price per night from

$114