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Chamberlain Holiday Rentals

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50 rentals in Chamberlain.
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Stunning Property, Ocean Views, Beautifully Decorated, Fireplace, Chef's Kitchen, holiday rental in Chamberlain

Stunning Property, Ocean Views, Beautifully Decorated, Fireplace, Chef's Kitchen

3 bedrooms
3 bathrooms
Sleeps 8
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Charming Woodsy Cottage - Ocean View with Monhegan Island, holiday rental in Chamberlain

Charming Woodsy Cottage - Ocean View with Monhegan Island

3 bedrooms
1 bathroom
Sleeps 5
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Large, Private Family Home Recently Renovated, holiday rental in Chamberlain

Large, Private Family Home Recently Renovated

3 bedrooms
2 bathrooms
Sleeps 6
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Former B&B - now the whole home is available as a weekly rental, holiday rental in Chamberlain

Former B&B - now the whole home is available as a weekly rental

5 bedrooms
5 bathrooms
Sleeps 12
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A Unique Experience!!, holiday rental in Chamberlain

A Unique Experience!!

2 bedrooms
1 bathroom
Sleeps 5
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Classic Waterfront Cottage with Private Cove and Gardens - Boothbay Harbor, holiday rental in Chamberlain

Classic Waterfront Cottage with Private Cove and Gardens - Boothbay Harbor

3 bedrooms
2 bathrooms
Sleeps 6
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East Boothbay Waterfront One room Condo.Waterview from in side this room, holiday rental in Chamberlain

East Boothbay Waterfront One room Condo.Waterview from in side this room

1 bedroom
1 bathroom
Sleeps 2
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Private Oceanfront Cottage, Private Sand Beach -Lighthouse one mile away, holiday rental in Chamberlain

Private Oceanfront Cottage, Private Sand Beach -Lighthouse one mile away

2 bedrooms
1 bathroom
Sleeps 3
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Tranquil And Peaceful Vacation Getaway Just Waiting To Welcome You, holiday rental in Chamberlain

Tranquil And Peaceful Vacation Getaway Just Waiting To Welcome You

2 bedrooms
1 bathroom
Sleeps 5
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Beautiful Antique Waterfront Property On Round Pond Harbor - Sleeps 7, holiday rental in Chamberlain

Beautiful Antique Waterfront Property On Round Pond Harbor - Sleeps 7

2 bedrooms
2 bathrooms
Sleeps 7
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Authentic Log Cabin on Damariscotta River W/ Dock and Moorings, holiday rental in Chamberlain

Authentic Log Cabin on Damariscotta River W/ Dock and Moorings

2 bedrooms
1 bathroom
Sleeps 4
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Your Windows To The Ocean, Lobstering Village, And Private Floating Dock!, holiday rental in Chamberlain

Your Windows To The Ocean, Lobstering Village, And Private Floating Dock!

2 bedrooms
1 bathroom
Sleeps 6
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Amazing sunsets/Cozy cottage/Ocean view/Hidden Gem near Boothbay Harbo, holiday rental in Chamberlain

Amazing sunsets/Cozy cottage/Ocean view/Hidden Gem near Boothbay Harbo

2 bedrooms
1 bathroom
Sleeps 4
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The Barn at Round Pond, holiday rental in Chamberlain

The Barn at Round Pond

1 bedroom
1 bathroom
Sleeps 2
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Cozy Detached Guest Cottage on Mill Pond, holiday rental in Chamberlain

Cozy Detached Guest Cottage on Mill Pond

1 bedroom
1 bathroom
Sleeps 3
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Tranquil!!  Oceanfront Sunsets with beach, pier,and deep water access, holiday rental in Chamberlain

Tranquil!! Oceanfront Sunsets with beach, pier,and deep water access

1 bedroom
1 bathroom
Sleeps 3
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Gorgeous Oceanfront Sunsets With Deep Water Access!, holiday rental in Chamberlain

Gorgeous Oceanfront Sunsets With Deep Water Access!

1 bedroom
1 bathroom
Sleeps 2
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Cozy Cottage with Freshwater Frontage & Saltwater View, holiday rental in Chamberlain

Cozy Cottage with Freshwater Frontage & Saltwater View

2 bedrooms
1 bathroom
Sleeps 4
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Best view in East  Boothbay , Maine - 4 Bedroom Oceanfront Cottage, holiday rental in Chamberlain

Best view in East Boothbay , Maine - 4 Bedroom Oceanfront Cottage

4 bedrooms
1 bathroom
Sleeps 8
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Charming Year Round Cape House On Pemaquid Loop – Walk To Lighthouse, holiday rental in Chamberlain

Charming Year Round Cape House On Pemaquid Loop – Walk To Lighthouse

3 bedrooms
2 bathrooms
Sleeps 6
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Pemaquid Point Cliff Road-3B/1B Cottage w/Fireplace-Steps to Lighthouse-Pet ok, holiday rental in Chamberlain

Pemaquid Point Cliff Road-3B/1B Cottage w/Fireplace-Steps to Lighthouse-Pet ok

3 bedrooms
1 bathroom
Sleeps 4
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Seaworthy- A Perfect Maine Coast Location, holiday rental in Chamberlain

Seaworthy- A Perfect Maine Coast Location

3 bedrooms
2 bathrooms
Sleeps 6
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Gorgeous sunsets on peaceful Linekin Bay coastal beach at low tide, dockfloat, holiday rental in Chamberlain

Gorgeous sunsets on peaceful Linekin Bay coastal beach at low tide, dockfloat

1 bedroom
1 bathroom
Sleeps 4
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Coastal Home on Muscongus Bay, holiday rental in Chamberlain

Coastal Home on Muscongus Bay

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Romantic Oceanfront Camp for Two, holiday rental in Chamberlain

Romantic Oceanfront Camp for Two

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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New listing! Oceanfront home w/ a wood stove, full kitchen, & stunning bay views, holiday rental in Chamberlain

New listing! Oceanfront home w/ a wood stove, full kitchen, & stunning bay views

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Waterfront cabin w/ ocean view, fireplace, & private dock, holiday rental in Chamberlain

Waterfront cabin w/ ocean view, fireplace, & private dock

2 bedrooms
1 bathroom
Sleeps 6
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Slow Down & Go Back in Time-Relax Completely in Our Maine Home, holiday rental in Chamberlain

Slow Down & Go Back in Time-Relax Completely in Our Maine Home

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Spend the Coming Summer in a Private Home in Round Pond, Maine, holiday rental in Chamberlain

Spend the Coming Summer in a Private Home in Round Pond, Maine

2 bedrooms
2 bathrooms
Sleeps 4
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Contemporary Cottage With Spectacular Ocean Views And Access, holiday rental in Chamberlain

Contemporary Cottage With Spectacular Ocean Views And Access

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Pemaquid Point Cottage Near Lighthouse,Two Bedrooms Ocean View, holiday rental in Chamberlain

Pemaquid Point Cottage Near Lighthouse,Two Bedrooms Ocean View

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Charming Home W/Harbor View: Walk to Resturants, Shops & Beach, holiday rental in Chamberlain

Charming Home W/Harbor View: Walk to Resturants, Shops & Beach

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Maine Coast House with Spectacular Ocean Views and Sandy Beach for Swimming, holiday rental in Chamberlain

Maine Coast House with Spectacular Ocean Views and Sandy Beach for Swimming

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Shearwater a uniquely charming Maine cottage near the rocky coast, holiday rental in Chamberlain

Shearwater a uniquely charming Maine cottage near the rocky coast

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Quiet and dog-friendly studio, walking distance to the harbor!, holiday rental in Chamberlain

Quiet and dog-friendly studio, walking distance to the harbor!

0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Dalton Cottage on Coast of Maine with Spectacular Views & Crashing Surf, holiday rental in Chamberlain

Dalton Cottage on Coast of Maine with Spectacular Views & Crashing Surf

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Classic Retro Cottage, holiday rental in Chamberlain

Classic Retro Cottage

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Mossy Glen Lodge  'Log Cabin' with a brook and hammock, holiday rental in Chamberlain

Mossy Glen Lodge 'Log Cabin' with a brook and hammock

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Finch Cottage, holiday rental in Chamberlain

Finch Cottage

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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The Loft Guest Cottage, holiday rental in Chamberlain

The Loft Guest Cottage

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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South Bristol Boathouse, holiday rental in Chamberlain

South Bristol Boathouse

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Maine Cottage, Mid-Coast Maine, holiday rental in Chamberlain

Maine Cottage, Mid-Coast Maine

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Open Floor-plan Home near Harbor, Beach and Lighthouse, holiday rental in Chamberlain

Open Floor-plan Home near Harbor, Beach and Lighthouse

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Boothbay Vacation home, holiday rental in Chamberlain

Beautiful Boothbay Vacation home

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Ocean Waterfront - Walk to Pemaquid Light, holiday rental in Chamberlain

Ocean Waterfront - Walk to Pemaquid Light

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Lobster Haven, holiday rental in Chamberlain

Lobster Haven

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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OceanView BonnieView, holiday rental in Chamberlain

OceanView BonnieView

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Light Filled, Woodsy Views, Atlantic Ocean Nearby - Classic Mid-Coast Cottage, holiday rental in Chamberlain

Light Filled, Woodsy Views, Atlantic Ocean Nearby - Classic Mid-Coast Cottage

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Charming Cottage just a short walk to Pemaquid Beach!, holiday rental in Chamberlain

Charming Cottage just a short walk to Pemaquid Beach!

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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NEW! Spacious Bristol House w/ Deck & Harbor Views, holiday rental in Chamberlain

NEW! Spacious Bristol House w/ Deck & Harbor Views

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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