We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Chamberlain Vacation Rentals

List your property
Owner log in
Check in
— / — / —
Check out
— / — / —
Guests
0 rooms, 2+ guests
Distance from
1 mi
Suitability
Show more
Bathrooms
Any
Amenities
Show more
Property type
Show more
Distinctive Features
Show more
50 rentals in Chamberlain.
Sort by:
Tripadvisor Sort
Stunning Property, Ocean Views, Beautifully Decorated, Fireplace, Chef's Kitchen, vacation rental in Chamberlain

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

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Charming Woodsy Cottage - Ocean View with Monhegan Island, vacation rental in Chamberlain

Charming Woodsy Cottage - Ocean View with Monhegan Island

3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Large, Private Family Home Recently Renovated, vacation rental in Chamberlain

Large, Private Family Home Recently Renovated

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Former B&B - now the whole home is available as a weekly rental, vacation rental in Chamberlain

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

5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
A Unique Experience!!, vacation rental in Chamberlain

A Unique Experience!!

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Classic Waterfront Cottage with Private Cove and Gardens - Boothbay Harbor, vacation rental in Chamberlain

Classic Waterfront Cottage with Private Cove and Gardens - Boothbay Harbor

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
East Boothbay Waterfront One room Condo.Waterview from in side this room, vacation rental in Chamberlain

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

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Private Oceanfront Cottage, Private Sand Beach -Lighthouse one mile away, vacation rental in Chamberlain

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

2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Tranquil And Peaceful Vacation Getaway Just Waiting To Welcome You, vacation rental in Chamberlain

Tranquil And Peaceful Vacation Getaway Just Waiting To Welcome You

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Beautiful Antique Waterfront Property On Round Pond Harbor - Sleeps 7, vacation rental in Chamberlain

Beautiful Antique Waterfront Property On Round Pond Harbor - Sleeps 7

2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Save time - get the best Chamberlain rentals sent straight to your email!
Authentic Log Cabin on Damariscotta River W/ Dock and Moorings, vacation rental in Chamberlain

Authentic Log Cabin on Damariscotta River W/ Dock and Moorings

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Amazing sunsets/Cozy cottage/Ocean view/Hidden Gem near Boothbay Harbo, vacation rental in Chamberlain

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

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
The Barn at Round Pond, vacation rental in Chamberlain

The Barn at Round Pond

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Cozy Detached Guest Cottage on Mill Pond, vacation rental in Chamberlain

Cozy Detached Guest Cottage on Mill Pond

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Tranquil!!  Oceanfront Sunsets with beach, pier,and deep water access, vacation rental in Chamberlain

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

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Your Windows To The Ocean, Lobstering Village, And Private Floating Dock!, vacation rental in Chamberlain

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

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Gorgeous Oceanfront Sunsets With Deep Water Access!, vacation rental in Chamberlain

Gorgeous Oceanfront Sunsets With Deep Water Access!

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Cozy Cottage with Freshwater Frontage & Saltwater View, vacation rental in Chamberlain

Cozy Cottage with Freshwater Frontage & Saltwater View

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Best view in East  Boothbay , Maine - 4 Bedroom Oceanfront Cottage, vacation rental in Chamberlain

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

4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Charming Year Round Cape House On Pemaquid Loop – Walk To Lighthouse, vacation rental in Chamberlain

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

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Pemaquid Point Cliff Road-3B/1B Cottage w/Fireplace-Steps to Lighthouse-Pet ok, vacation rental in Chamberlain

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

3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Seaworthy- A Perfect Maine Coast Location, vacation rental in Chamberlain

Seaworthy- A Perfect Maine Coast Location

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Gorgeous sunsets on peaceful Linekin Bay coastal beach at low tide, dockfloat, vacation rental in Chamberlain

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

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Coastal Home on Muscongus Bay, vacation rental in Chamberlain

Coastal Home on Muscongus Bay

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Romantic Oceanfront Camp for Two, vacation rental in Chamberlain

Romantic Oceanfront Camp for Two

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
New listing! Oceanfront home w/ a wood stove, full kitchen, & stunning bay views, vacation rental in Chamberlain

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

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Waterfront cabin w/ ocean view, fireplace, & private dock, vacation rental in Chamberlain

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

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Slow Down & Go Back in Time-Relax Completely in Our Maine Home, vacation rental in Chamberlain

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

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Spend the Coming Summer in a Private Home in Round Pond, Maine, vacation rental in Chamberlain

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

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Contemporary Cottage With Spectacular Ocean Views And Access, vacation rental in Chamberlain

Contemporary Cottage With Spectacular Ocean Views And Access

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Pemaquid Point Cottage Near Lighthouse,Two Bedrooms Ocean View, vacation rental in Chamberlain

Pemaquid Point Cottage Near Lighthouse,Two Bedrooms Ocean View

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Charming Home W/Harbor View: Walk to Resturants, Shops & Beach, vacation rental in Chamberlain

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

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Maine Coast House with Spectacular Ocean Views and Sandy Beach for Swimming, vacation rental in Chamberlain

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

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Shearwater a uniquely charming Maine cottage near the rocky coast, vacation rental in Chamberlain

Shearwater a uniquely charming Maine cottage near the rocky coast

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Quiet and dog-friendly studio, walking distance to the harbor!, vacation rental in Chamberlain

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

0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Dalton Cottage on Coast of Maine with Spectacular Views & Crashing Surf, vacation rental in Chamberlain

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

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Classic Retro Cottage, vacation rental in Chamberlain

Classic Retro Cottage

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Mossy Glen Lodge  'Log Cabin' with a brook and hammock, vacation rental in Chamberlain

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

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Finch Cottage, vacation rental in Chamberlain

Finch Cottage

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection
The Loft Guest Cottage, vacation rental in Chamberlain

The Loft Guest Cottage

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection
South Bristol Boathouse, vacation rental in Chamberlain

South Bristol Boathouse

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Maine Cottage, Mid-Coast Maine, vacation rental in Chamberlain

Maine Cottage, Mid-Coast Maine

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection
Open Floor-plan Home near Harbor, Beach and Lighthouse, vacation rental in Chamberlain

Open Floor-plan Home near Harbor, Beach and Lighthouse

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Beautiful Boothbay Vacation home, vacation rental in Chamberlain

Beautiful Boothbay Vacation home

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
Check in
Check out
Payment Protection
Ocean Waterfront - Walk to Pemaquid Light, vacation rental in Chamberlain

Ocean Waterfront - Walk to Pemaquid Light

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection
Lobster Haven, vacation rental in Chamberlain

Lobster Haven

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
Check in
Check out
Payment Protection
OceanView BonnieView, vacation rental in Chamberlain

OceanView BonnieView

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Payment Protection
Light Filled, Woodsy Views, Atlantic Ocean Nearby - Classic Mid-Coast Cottage, vacation rental in Chamberlain

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

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection
Charming Cottage just a short walk to Pemaquid Beach!, vacation rental in Chamberlain

Charming Cottage just a short walk to Pemaquid Beach!

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
NEW! Spacious Bristol House w/ Deck & Harbor Views, vacation rental in Chamberlain

NEW! Spacious Bristol House w/ Deck & Harbor Views

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
Payment Protection
PreviousNext
1
Frequently Asked Questions about Chamberlain