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Compare 356 Vacation Homes in Chamberlain with updated reviews, rates, and availability.

Dog-friendly beach house with WiFi, private washer/dryer, deck, beautiful views
9.4 out of 10, Exceptional, (25)
"This is a great home with lots of room, natural light, comfortable bedrooms and a back deck we'd spend hours on in the evenings. Having a full bedroom and bathroom on the first floor and the two bedrooms and bathrooms upstairs also gave everyone privacy and downtime. The area is really quiet and walking distance from a path that runs alongside the water. The home is comfortable and roomy enough that being rained in for a day is no problem, and getting out to surrounding places is easy. "
Dog-friendly beach house with WiFi, private washer/dryer, deck, beautiful views
Beautiful Antique Waterfront Property On Round Pond Harbor - Sleeps 7
10.0 out of 10, Exceptional, (60)
"Steep and narrow steps to bedrooms. We Are older but rented it anyway and are so glad we did. The place is so peaceful, beautiful, so well appointed and decorated. We had to be forced out with threats of legal action 😁"
Beautiful Antique Waterfront Property On Round Pond Harbor - Sleeps 7
Beachfront Delight with detached guesthouse, sunset views & private beach access
9.4 out of 10, Exceptional, (8)
"Easy access property! Very private! The notes specify no A/C but it does not mention heat. There are baseboard electric heaters in the main house and cabin."
Beachfront Delight with detached guesthouse, sunset views & private beach access
More then a Motel With Garden , Renovated Rooms at heart of Boothbay
2.0 star property
The price is AED 286
AED 512 total
includes taxes & fees
22 Sep - 23 Sep
More then a Motel With Garden , Renovated Rooms at heart of Boothbay
Newly Renovated Haven w/ Deck, Near Downtown: Walk to Shops, Dining & Marina
9.4 out of 10, Exceptional, (46)
"We had a two-night stay. And since we were so close to the harbor, it made for easy walks to the points of interest nearby; easy walk to the harbor. We could see the harbor from out the windows. We cooked on the newer clean grill. You need to sign into your own Roku account to use the TV which we did to see the Olympics."
Newly Renovated Haven w/ Deck, Near Downtown: Walk to Shops, Dining & Marina
Make Shimmering River Retreat your Maine Coastal getaway!
9.6 out of 10, Exceptional, (30)
"We have rented many properties for our yearly family vacation but this was by far our favorite! We've already rebooked for next year. The location, the size of the property, the pool, the outdoor areas... everything was amazing! The adults loved the deepwater dock, the kayaks and canoe. The little kids loved the pool. There were many places to go visit locally but we were able to come back to the peace and tranquility of the house. The guest cottage was a big hit for the grandkids!"
Make Shimmering River Retreat your Maine Coastal getaway!
Downtown Boothbay Harbor, 2-Story Cottage
9.8 out of 10, Exceptional, (13)
"House was a short walk to Boothbay Harbor. Owners were great on communication with us prior to check in. House condition was good. It is need in need of a paint job and a few repairs. The price for a 2 night stay was great. Only issue for me was that bathroom has no door and located upstairs in bedroom. It only had a light weight curtain. So when my spouse or myself had to use it during the night turning the light on in the bathroom woke up the other person. So bring a nightlight to plug in...
The price is AED 536
AED 1,117 total
includes taxes & fees
6 Oct - 7 Oct
Downtown Boothbay Harbor, 2-Story Cottage
Enjoy the stunning views while relaxing on the deck at East Ledge Cottage
10.0 out of 10, Exceptional, (46)
"This place is so peaceful! Being able to see the water from just about every room. The pics in listing can’t even begin to show the beauty of this spot! Super clean and a kitchen with great utensils and pans, anything you need! Would stay again!"
Enjoy the stunning views while relaxing on the deck at East Ledge Cottage
Waterfront Cottage on Tidal Cove with Dock
9.8 out of 10, Exceptional, (41)
"I wanted to stay in Maine for 3 weeks - I chose this location so I could be sometimes by myself and sometimes with friends. From this location, there is a lot to do locally as well as within 1 hour drive if desired. About 40 minutes to nearest Amtrak station in Brunswick if friends are visiting. Locally - many preserves to walk, kayak/paddleboard at house, minutes to Boothbay Harbor - schooner and wildlife boats, restaurants. This house was great for me as it was not too big when I was by...
Waterfront Cottage on Tidal Cove with Dock
Captain's House Guest Room Suite
6.6 out of 10, (7)
"Made a mistake with the rooms! Dimitri was very calm about the situation and helped rectify it immediately."
Captain's House Guest Room Suite
Cozy Cottage with Ocean Views and Dog-Friendly Charm
2.0 star property
10.0 out of 10, Exceptional, (1)
"Liked having the cottage to our selves and home like feeling. The only thing that was not there was a outdoors firepit or fireplace to enjoy more of the outdoors but we loved it and might even try to get back soon"
Cozy Cottage with Ocean Views and Dog-Friendly Charm
Stunning oceanfront cottage w/ private deck and Atlantic views
9.2 out of 10, Wonderful, (46)
"Clean, lovely view, inside twisting, narrow stairs not great for little ones or older ones with bad knees. Deck is off both upper bedrooms."
Stunning oceanfront cottage w/ private deck and Atlantic views
Slow Down & Go Back in Time-Relax Completely in Our Maine Home
9.6 out of 10, Exceptional, (63)
"An immaculate well appointed cottage that was an absolute delight. Close to everything, including Colonial Pemaquid, Pemaquid Beach and the lighthouse."
Slow Down & Go Back in Time-Relax Completely in Our Maine Home
Private Oceanfront Home on 10 Acres -- 2 Fireplaces, 4 Decks & Grill
8.8 out of 10, Excellent, (19)
"the house location and the house itself are simply magnificent. The house could stand a few improvements. The deck furniture is simply terrible. The Small table and the chairs are old and rusted. One chair was totally unusable. This is our second stay there and are planning on another stay. We are hoping for a new deck set."
Private Oceanfront Home on 10 Acres -- 2 Fireplaces, 4 Decks & Grill
TWO BEDROOM Guest Suite in the Heart of Bath
6.6 out of 10, (4)
"We enjoyed our stay if it was mine I would make the living area have more comfortable seating less desks Maybe a sink in kitchen area"
The price is AED 624
AED 997 total
includes taxes & fees
22 Sep - 23 Sep
TWO BEDROOM Guest Suite in the Heart of Bath
Multi-unit with oar & boat house with private dock & kayaks
9.0 out of 10, Wonderful, (21)
"Stayed for a week. You can’t beat the location! Fabulous spot with a dock and deck right on the Harbor. 5 min walk into town. The property is a great set up if you’ve got a large party. We were 10 and it was perfect. There are a few things that need some work… Only one bathroom had a bathmat and the 2nd floor shower in the main house is difficult to navigate without drenching the floor with its multitude of curtains and no shelf or hanging caddy to put soap and shampoo. The bedrooms, including...
Multi-unit with oar & boat house with private dock & kayaks
Quintessential Maine Oceanfront home
10.0 out of 10, Exceptional, (70)
"Had a wonderful time at the home. The views are just beautiful!"
Quintessential Maine Oceanfront home
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
Admiral's Quarters - Room 12
10.0 out of 10, Exceptional, (2)
"This place was an amazing location. Very clean. Just what we needed for the night. The host was very helpful. Would definitely recommend. We will definitely stay here again when we go to Boothbay. "
Admiral's Quarters - Room 12
2 bedroom 1 bath, large deck and dock, on the water in peaceful cove, Year
9.8 out of 10, Exceptional, (16)
"Best part of this place is the dock where you can sit and watch the tide come in and go out. When it's out you see all kinds of birds (including one very elegant egret.). When it's in you can swim and kayak."
2 bedroom 1 bath, large deck and dock, on the water in peaceful cove, Year
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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

Appalachee Pond Waterfront Cottage | Decks, Sunroom, Dock with Kayaks & Canoe
9.6 out of 10, Exceptional, (27)
"This house was amazing. It was way better than we expected after looking through the pictures online. The outdoor space and the house itself are beautiful and the pictures do it zero justice. We were worried at first about the lack of AC, but the house cooled right down once we opened the windows let the air in. I highly recommend this place if you’re looking to visit Boothbay. It was so close to the main area, but you couldn’t even tell- it felt like you were immersed in nature."
Appalachee Pond Waterfront Cottage | Decks, Sunroom, Dock with Kayaks & Canoe
Hidden Gem on Westport Island
10.0 out of 10, Exceptional, (96)
"This house was the perfect spot for a weekend getaway with friends. Carol was very responsive and answered all questions in a timely manner. House was well equipped with everything that we needed. Highly recommend staying here!"
Hidden Gem on Westport Island
Unique oceanfront home with a deck, tons of natural light, & amazing views
8.6 out of 10, Excellent, (49)
"Beautiful property. Saw seals from living room catching fish. Front door did not lock but it’s a safe neighborhood but a bit isolated. Kitchen is well equipped for cooking. Laundry facilities were a great help! Gorgeous views of the water and excellent service and communication."
Unique oceanfront home with a deck, tons of natural light, & amazing views
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.