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Compare 423 Vacation Homes in Woolwich 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.
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)
"Loved it! In"
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, (67)
"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
Lakeside retreat in Central Maine
Beach

Lakeside retreat in Central Maine

9.8 out of 10, Exceptional, (79)
"I can't explain the ease and how helpful the host was. We were traveling from a long distance for this. The host was helpful with late check in. The house was well maintained and clean everywhere. You get everything you need. The wifi is also fast. I wish they did provide some body wash and some extra stuff. No complaints at all. It was a memorable stay"
Lakeside retreat in Central Maine
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
Coastal Cottage in fishing Village
Cottageportch

Coastal Cottage in fishing Village

9.2 out of 10, Wonderful, (5)
"My wife and I can not say enough good. Everything was fantastic we can't wait to visit again , everyone in the area were very nice the location was incredible.tjanknyou very much for the pleasant stay"
Coastal Cottage in fishing Village
Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly
View of house from lake

Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly

10.0 out of 10, Exceptional, (237)
"Everything that was promised was fulfilled. Host & caretaker were available and great to deal with. House was welcoming and comfortable in this cold-weather visit. We’d love to return in summer, the lake access clearly is wonderful."
Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly
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 SAR 620
SAR 1,228 total
includes taxes & fees
14 Jan - 15 Jan
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
Charming ocean-view cottage just 10 minutes from downtown Freeport shops
Living area

Charming ocean-view cottage just 10 minutes from downtown Freeport shops

2.0 star property
10.0 out of 10, Exceptional, (1)
"As you enter the house, you are entering the kitchen and looking at the most wall sized widow framed picturesque ocean waterfront view with islands included. We had two children with us and there was a has sack storage box filled with toys and a midsized toy kitchen that kept the children busy. The accommodations were cozy and homelike . We are already contemplating a warmer season return to enjoy the oceanfront amenities!"
Charming ocean-view cottage just 10 minutes from downtown Freeport shops
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!"
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
Full sized home
Private kitchen

Full sized home

9.6 out of 10, Exceptional, (24)
"The house is very clean, and it's very well situated. There are plenty of room in and out. Will come again."
Full sized home
Amazing riverfront home with private deck, views, private dock, & fireplace

Amazing riverfront home with private deck, views, private dock, & fireplace

9.4 out of 10, Exceptional, (40)
"Beautiful place! Perfect fit for us"
Amazing riverfront home with private deck, views, private dock, & fireplace
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
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 Woolwich

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
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, (97)
"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
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
THE GILLS GROUP has two additional cottages available for larger groups

PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room

10.0 out of 10, Exceptional, (99)
"This property is stunning, and the view is spectacular. If this were my house, I’d never leave! We had a fabulous time. "
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
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.