Photo by Bill Boyd

Holiday Homes in Boothbay

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Featured Holiday Homes in Boothbay

Oceanfront Cabin-Castle in Maine Woods
9.6 out of 10, Exceptional, (5)
"We enjoyed a week of beautiful sun rises, the lulling waves, and peaceful walks in Reid state park. If you are looking for a recharge of your nature battery, this is it. "
Oceanfront Cabin-Castle in Maine Woods
Hidden Gem on Westport Island
10.0 out of 10, Exceptional, (97)
"Hidden gem is the perfect way to describe this amazing property at 19 Rocky Rd on beautiful Westport Island! We stayed 2 nights and wished we could have stayed longer! Next time! We feel very blessed by the whole experience! Thank you owners!"
Hidden Gem on Westport Island
Waterfront Cottage on Tidal Cove with Dock
9.8 out of 10, Exceptional, (42)
"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
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
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
Newly Renovated Haven w/ Deck, Near Downtown: Walk to Shops, Dining & Marina
9.4 out of 10, Exceptional, (47)
"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
Enjoy the stunning views while relaxing on the deck at East Ledge Cottage
10.0 out of 10, Exceptional, (47)
"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
The Sea Eagle - Luxury 5 BR Waterfront Home in Boothbay Harbor
10.0 out of 10, Exceptional, (3)
"Loved our stay. Walking distance to everything. Kids loved the kayaks & dock. We loved having coffee on the harbor every morning. Plenty of room for multiple families. "
The Sea Eagle - Luxury 5 BR Waterfront Home in Boothbay Harbor
Full sized home
9.6 out of 10, Exceptional, (19)
"We only stayed a night but everything was thoughtfully provided-very comfortable beds, week equipped kitchen and great information about places to eat and order food. Thank you for sharing this home!"
The price is AU$594
includes taxes & fees
1 Oct - 2 Oct
Full sized home
Lowell's Getaway. Kayaking, beaches, dining and AC from this water view home.
9.6 out of 10, Exceptional, (31)
"Thoroughly enjoyed this house.Home had a Great layout . Clean . Beds comfortable . Would stay here again!"
Lowell's Getaway. Kayaking, beaches, dining and AC from this water view home.
TWO BEDROOM Guest Suite in the Heart of Bath
6.4 out of 10, (5)
"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 AU$401
includes taxes & fees
1 Oct - 2 Oct
TWO BEDROOM Guest Suite in the Heart of Bath
The Coal Shack: Dog-Friendly Harborfront Studio in Downtown Boothbay
10.0 out of 10, Exceptional, (145)
"Loved the Coal Shack! Beautiful place with a great view! Perfectly situated. Easy to come and go. Shower was amazing! Would definitely recommend!"
The Coal Shack: Dog-Friendly Harborfront Studio in Downtown Boothbay
Nicest Waterfront in Maine w/ Private Beach!
9.6 out of 10, Exceptional, (35)
"Well-situated gorgeous space for several families to gather, eat good food, swim, kayak, and enjoy lovely views from every window."
Nicest Waterfront in Maine w/ Private Beach!
Waterfront Estate in Popham Beach
9.8 out of 10, Exceptional, (7)
"Our sojourn at Stone House Manor was peaceful, beautiful, and comfortable! We were a collection of foodies and cooks, and the well stocked kitchen was a tremendous asset, as we ate in almost every night. Rachael was always available to answer questions, and the owner Jane could not have been more helpful. For example, they brought an air mattress that we were able to set up in one of the studies to accommodate our large party. The house was well appointed, and it was truly a home away from...
Waterfront Estate in Popham Beach
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
Cottage in Edgecomb - Waterfront Holiday Getaway
10.0 out of 10, Exceptional, (22)
"The property inside, I would say, was renovated recently . Decorated very nicely and was organized. The queen bedroom was comfortable. My wife and I stayed for 4 nights going south to Portland and north to Arcadia and bar harbor and around Wiscasset Boothbay and Edgecomb the other days.Th only thing is the outside could use a deck and a walkway and a drive way. Nancy the host was very communicative and nice. Thanks for the use of your beautiful home!"
Cottage in Edgecomb - Waterfront Holiday Getaway
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
Cundy’s Harbor
10.0 out of 10, Exceptional, (2)
"We had a nice and relaxing time. Everything is a little drive but the area is so pretty with the tides changing, the drive was always a nice one. I know Ac is not the norm up in Maine, but the downstairs unit served us well. I was wishing for a ac unit upstairs that fiirst night but then it cooled down and was much more comfortable the rest of the trip. We used to have chickens so i was a bit bummed when the coop was empty but there is the cutest duck that lives next door! I know that chickens...
The price is AU$902
includes taxes & fees
1 Oct - 2 Oct
Cundy’s Harbor
Oceanfront, views from every room! Spacious midcoast retreat with private dock
10.0 out of 10, Exceptional, (20)
"Wonderful location and outstanding accommodations. "
Oceanfront, views from every room! Spacious midcoast retreat with private dock
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Other property types in Boothbay

Lakefront gem with 350' of private lake on 2 acres with 2 kayaks & seasonal dock
7.8 out of 10, Good, (10)
"Friends gathered in Boothbay for birding and exploring. This lovely older home, which appears to be a generational family getaway, was the perfect spot to relax and stay in. It’s tucked away from the town in a rustic setting but an easy few minutes to drive to downtown. It only has one bathroom, but the house had enough amenities and space to spread out. The rooms were comfortable and outfitted with acs in each, which was appreciated. The location is central to get to downtown Boothbay and...
Lakefront gem with 350' of private lake on 2 acres with 2 kayaks & seasonal dock
1 room luxury ocean front studio cottage
9.6 out of 10, Exceptional, (141)
"3 words..... Wlll come back"
1 room luxury ocean front studio cottage
Unique oceanfront home with a deck, tons of natural light, & amazing views
8.6 out of 10, Excellent, (50)
"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.