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Compare 312 Vacation Homes in Chamberlain with updated reviews, rates, and availability.

Newly renovated 3 bedroom, 2 bath bungalow, walking distance to downtown.
Newly renovated 3 bedroom, 2 bath bungalow.

Newly renovated 3 bedroom, 2 bath bungalow, walking distance to downtown.

10.0 out of 10, Exceptional, (70)
"Jaymes house had everything we could’ve need for our stay in boothbay. Well equipped for travelers most towels and bedding in the house appear to be new. Very responsive and accommodating house, perfect size for 2-3 couples to enjoy a weekend close to the harbor. "
Newly renovated 3 bedroom, 2 bath bungalow, walking distance to downtown.
The Perch - A cozy cottage minutes from Tenants Harbor, with water access!
Welcome to the Perch!

The Perch - A cozy cottage minutes from Tenants Harbor, with water access!

10.0 out of 10, Exceptional, (17)
"This property was amazing! Abby was in contact anytime i needed anything. Will definitely contact again if we choose to go back to visit!!"
The Perch - A cozy cottage minutes from Tenants Harbor, with water access!
Private Oceanfront Cottage, Private Sand Beach -Lighthouse one mile away
Beach

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

10.0 out of 10, Exceptional, (90)
"Beautiful location, really enjoyed the stay. The stairs are a challenge especially with no landing at the top. Didn't receive any notification about check-in and I got no answer when I called but when I checked the door was unlocked and keys were on the table. Everything was very clean and the kitchen was well equipped. "
Private Oceanfront Cottage, Private Sand Beach -Lighthouse one mile away
Oceanfront Cabin-Castle in Maine Woods
Fall View from Porch

Oceanfront Cabin-Castle in Maine Woods

10.0 out of 10, Exceptional, (11)
"Absolutely loved this property! My family and I enjoyed every minute of our stay! Listening to the waves crashing on the rocks, hanging out by the fire and just relaxing made for the perfect after Christmas getaway! I look forward to coming again! Highly recommend "
Oceanfront Cabin-Castle in Maine Woods
Slow Down & Go Back in Time-Relax Completely in Our Maine Home
Sea-air nourishes our flowerbox blossoms all summer--

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

9.6 out of 10, Exceptional, (68)
"I enjoyed my stay over Thanksgiving weekend at Martha's New Harbor, Maine home. It's charming with lots of attractive features. My favorite was the fireplace in the living room which I used all three nights. Thanks, Keith"
Slow Down & Go Back in Time-Relax Completely in Our Maine Home
Bayfront home with 270-degree views, large deck & porch - near Popham Beach

Bayfront home with 270-degree views, large deck & porch - near Popham Beach

8.2 out of 10, Very Good, (29)
"The house is beautiful, comfortable and was pristine when we checked in. Decks and screened porch are wonderful. The kids loved the 3rd floor bedroom space, and it was fabulous being so close to Popham Beach. Definitely recommend. Kitchen on 2nd floor ... so have some strong helpers to bring in groceries ;)"
Bayfront home with 270-degree views, large deck & porch - near Popham Beach
Dog-friendly bay view home - water views, dock access & Linekin Bay Resort fun

Dog-friendly bay view home - water views, dock access & Linekin Bay Resort fun

5.6 out of 10, (5)
"The shared driveway was a challenge and the hike from the driveway to the house had was also a challenge. Additionally the window in one of the bathrooms did not work, the dishwasher was not secured and tilted when you put dishes in, one of the commodes ran constantly unless you jiggle. The kitchen garbage can is broken."
Dog-friendly bay view home - water views, dock access & Linekin Bay Resort fun
Don't miss the Pumpkin Festival weekend filled with lobster dinners and oysters
Front Yard

Don't miss the Pumpkin Festival weekend filled with lobster dinners and oysters

9.0 out of 10, Wonderful, (73)
"It was so nice to be next door to family to celebrate our uncle’s 90th birthday. We enjoyed staying in a house with a lot of history. "
Don't miss the Pumpkin Festival weekend filled with lobster dinners and oysters
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
Exterior

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

10.0 out of 10, Exceptional, (20)
"We usually rent right near our relatives closer to Newcastle, but there was a problem with heat in property so we needed a new rental to move into and “Otterly getaway” was willing to rent to us the day before they technically were available which was good for us. The kitchen of the getaway is just perfect for cooking side dishes for our large family Thanksgiving that was just about 20 minutes a way. We slept in the king bed and it was excellent sleeping. The heating system kept us also very...
The price is AED 606
AED 1,197 total
includes taxes & fees
14 Jan - 15 Jan
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
Luxury Carriage House a short stroll from town!
Private kitchen

Luxury Carriage House a short stroll from town!

2.0 star property
10.0 out of 10, Exceptional, (5)
"Amazing location and beautiful little property. Everything was immaculate and welcoming, and we felt so taken care of, down to the small touches like just the coffee we like! Communication was great and timely, too. We'll definitely be back next time we are in Maine!"
The price is AED 1,466
AED 2,230 total
includes taxes & fees
13 Jan - 14 Jan
Luxury Carriage House a short stroll from town!
Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views

Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views

9.2 out of 10, Wonderful, (81)
"This house is in perfect spot in Boothbay Harbor. Easy walk to town, right on the water. Everything about the house was perfect and exactly what we needed. "
Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views
Century-old oceanfront home with wraparound porch - walk downtown, dogs OK

Century-old oceanfront home with wraparound porch - walk downtown, dogs OK

8.8 out of 10, Excellent, (35)
"Our party of 8 enjoyed our stay. The house is well equipped and stocked to get you started. Conveniently located to town and the Botanical Gardens. Plenty of outside space for kids to run around and play. It has a beautiful view of the cove but is very rocky. This didn't stop us from hunting hermit crabs and catching fish. The house is old but that gives it the Maine charm. "
Century-old oceanfront home with wraparound porch - walk downtown, dogs OK
Expansive Modern Home w/ Ocean View, Gorgeous Garden & Multiple Sitting Areas

Expansive Modern Home w/ Ocean View, Gorgeous Garden & Multiple Sitting Areas

8.4 out of 10, Very Good, (23)
"Spacious house with nice views."
Expansive Modern Home w/ Ocean View, Gorgeous Garden & Multiple Sitting Areas
Newly Renovated Haven w/ Deck, Near Downtown: Walk to Shops, Dining & Marina

Newly Renovated Haven w/ Deck, Near Downtown: Walk to Shops, Dining & Marina

9.4 out of 10, Exceptional, (51)
"There were four of us so we each had a bedroom. We have been friends since 1955!!! It was a wonderful getaway! "
Newly Renovated Haven w/ Deck, Near Downtown: Walk to Shops, Dining & Marina
Well-located, dog-friendly home - walk to footbridge & Barrett Park

Well-located, dog-friendly home - walk to footbridge & Barrett Park

9.2 out of 10, Wonderful, (30)
"perfect for our weekend away. Will plan to return."
Well-located, dog-friendly home - walk to footbridge & Barrett Park
Boothbay Harbor Home with Water Views | Near Dining & Whale Watching

Boothbay Harbor Home with Water Views | Near Dining & Whale Watching

10.0 out of 10, Exceptional, (62)
"Overall everything was fine. The one negative was the internet did not work even with communication from owner texting option to correct. None repaired the issue. Would return as close to extended family."
Boothbay Harbor Home with Water Views | Near Dining & Whale Watching
Oceanfront home & guesthouse w/ incredible ocean views, deck & location

Oceanfront home & guesthouse w/ incredible ocean views, deck & location

9.6 out of 10, Exceptional, (65)
"We loved this place. Even better in person than the pictures. Gorgeous setting on Ocean Point in a quiet neighborhood. Very nicely appointed, it meets all your needs and when the thermostat acted up the property manager was quick to respond and provide space heaters until hvac could come the next morning. We highly recommend and will stay here again. "
Oceanfront home & guesthouse w/ incredible ocean views, deck & location
The Coal Shack: Dog-Friendly Harborfront Studio in Downtown Boothbay

The Coal Shack: Dog-Friendly Harborfront Studio in Downtown Boothbay

10.0 out of 10, Exceptional, (150)
"I love coming to Boothbay. I have family in the area and to be in the harbor was just perfect!"
The Coal Shack: Dog-Friendly Harborfront Studio in Downtown Boothbay
Secluded waterfront home with firepit, gas grill, kayaks, dock, balcony, & patio

Secluded waterfront home with firepit, gas grill, kayaks, dock, balcony, & patio

9.8 out of 10, Exceptional, (12)
"The location was perfect for traveling the coast and yet secluded enough for peace and quiet. Easy to work with property management as well."
Secluded waterfront home with firepit, gas grill, kayaks, dock, balcony, & patio
Enjoy spectacular views of Lobster Cove. Large yard, EV charger & dog friendly.
Outdoor dining

Enjoy spectacular views of Lobster Cove. Large yard, EV charger & dog friendly.

10.0 out of 10, Exceptional, (12)
"This property was exactly as advertised. It was clean, up to date with modern appliances, clean linens and towels. It was well stocked. Beautiful view of the cove from the front deck. My grandchildren loved being near Barrett Park. Property contact was prompt with answers. A very relaxing stay. We would definitely book again. "
Enjoy spectacular views of Lobster Cove. Large yard, EV charger & dog friendly.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Chamberlain

East Boothbay Waterfront One room Condo.Waterview from in side this room
View of Pristine Linekin Bay.Common area dock is on the left.

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

9.8 out of 10, Exceptional, (127)
"perfect love to be back next year"
East Boothbay Waterfront One room Condo.Waterview from in side this room
The Perch - A cozy cottage minutes from Tenants Harbor, with water access!
Welcome to the Perch!

The Perch - A cozy cottage minutes from Tenants Harbor, with water access!

10.0 out of 10, Exceptional, (17)
"This property was amazing! Abby was in contact anytime i needed anything. Will definitely contact again if we choose to go back to visit!!"
The Perch - A cozy cottage minutes from Tenants Harbor, with water access!
A Charming Waterfront Cottage with Touches of Elegance
This 44 foot porch runs the width of the house with panoramic views of the water

A Charming Waterfront Cottage with Touches of Elegance

10.0 out of 10, Exceptional, (98)
"We were having a delightful stay until we noticed that there was no heat but from the fire place. Unfortunately, we had to leave in the middle of our stay. Vrbo gave us a refund. I would stay there again. Lovely and sunny. Excellent Property Manager."
A Charming Waterfront Cottage with Touches of Elegance
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.