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Chamberlain Rentals

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Chamberlain Rentals

176 Houses

M&M Cottage - Walk to Town from this Roomy Boothbay Harbor House, Pet Friendly

Boothbay Harbor house

2 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$160

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Lakefront Gem - 350’ of Private Lake & 2 Acres, 2 Kayaks Provided!

Boothbay house

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$141

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Amazing Spring Special - Book Now! Private Pool and Dock

Boothbay Harbor cottage

7 bedrooms / 4 bathrooms / sleeps 14

Price per night from

$978

1 / 46

The Loft Guest Cottage

New Harbor house

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 58 minutes

Price per night from

$196

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Quintessential Maine! Green Gables Oceanfront 4BR Cottage w/ Private Beach

Friendship house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$169

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4BR Farmhouse + 1BR Cottage w/ New England Charm – Walk to Harbor

South Bristol house

5 bedrooms / 2 bathrooms / sleeps 11

Price per night from

$208

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Oceanfront 2BR Cottage on Wooded Half Acre w/ Ocean View

East Boothbay cottage

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$100

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Romantic Crow’s Nest Hideaway with Deck and Treetop Vistas – Walk to Downtown

Boothbay Harbor apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$78

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Doc`s_Place_Southport

Southport house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$293

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2BR Vintage Sprucewold Cabin w/ Crooked Pine Float Access

Boothbay Harbor log cabin

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$107

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Oar Island

Bremen cottage

3 bedrooms / 1 bathroom / sleeps 8

“perfect” We love Oar Island. It is the perfect vacation place for families with children of different ages, or just a couple. There is hiking, sunning, relaxation, but mostly what we love about Oar Island is the isolation. It is an adventure as well,

Price per night from

$245

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New England 1890 House with part water view

Boothbay Harbor apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$130

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New 2BR Timber Cottage —Private Retreat w/ Trails to Pond

Boothbay cottage

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$102

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Beautiful New 1BR Condo w/ River Views at Sheepscot Harbor Resort

Edgecomb apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$78

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Oceanfront Log Cabin, 1BR Haven w/ Loft, Sunroom, Swim Inlet & Stunning Views

Squirrel Island log cabin

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$159

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Mavooshen Retreat at Sprucewold, Private Beach Access, Minutes to Downtown

Boothbay Harbor log cabin

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$93

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Vintage, log cabin in the woods w/ beach club access (about a mile away)!

Boothbay Harbor house

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 3 minutes

Price per night from

$80

1 / 0

Charming water view home overlooking Mill Cove w/ a large deck - near town

Boothbay Harbor house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 3 minutes

Price per night from

$124

1 / 0

Oceanfront contemporary home with stunning island and lighthouse views

Southport house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 3 minutes

Price per night from

$169

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"Top of The World Vista" Edgecomb Cottage!

Edgecomb studio

Studio / 1 bathroom / sleeps 4

Responds fast! avg. 39 minutes

Price per night from

$229

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The Timber House

Cushing house

1 bedroom / 2 bathrooms / sleeps 8

Price per night from

$323

1 / 14

Laughton House & Cottages - Cottage

New Harbor cottage

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 19 minutes

Price per night from

$149

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Beautiful log cabin w/ forest views & wrap-around deck - close to town & beach!

Boothbay Harbor house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 hours 54 minutes

Price per night from

$210

1 / 0

Boothbay Harbor Penthouse- In Heart of Downtown with Harbor Views

Boothbay Harbor apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$354

1 / 24

Ledge_The_Southport

Newagen house

3 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$332

1 / 17

Classic 3BR House with New Kitchen – Walk to East Boothbay

East Boothbay house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$144

1 / 28

Responds fast! avg. 3 hours 3 minutes

Price per night from

$112

1 / 0

Family Friendly Shoreside 5BR w/ Island View, Near Boothbay Harbor & Downtown

Southport house

5 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$709

1 / 30

Discover a Family Tradition on Linekin Bay

Bayville house

6 bedrooms / 3 bathrooms / sleeps 16

Price per night from

$898

1 / 4

East Side Cove - At the Head of the Harbor with Dock, Walk to Town

Boothbay Harbor house

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$294

1 / 36

18 School Street Boothbay Harbor, ME

Boothbay Harbor house

3 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 1 hour 48 minutes

Price per night from

$200

1 / 16

Cozy 3BR Lobstermen’s Cottage - Large Deck w/ BBQ, Walk to Beach & Village

Boothbay Harbor house

3 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$144

1 / 24

4BR, 3.5BA East Boothbay Oceanfront Home with Deepwater Dock

East Boothbay house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$209

1 / 25

New 1BR Riverfront Condo in Sheepscot Harbour - Walk to Famed Seafood Eatery

Edgecomb apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$78

1 / 24

NEW LISTING! Dog-friendly cottage w/hot tub, backyard & bay view - near downtown

Boothbay Harbor house

4 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$174

1 / 0

Ledgemere_Cottage_Southport

Southport house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$319

1 / 27

Cozy_Cottage_Southport_Island

Southport house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$193

1 / 17

Snug Harbor: Historic 1BR, 1BA Boothbay Harbor Cottage w/Antique Decor

Boothbay Harbor apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$78

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