A lighthouse on a wooden pier extending into a body of water, surrounded by vegetation.

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Woolwich vacation homes

A backyard with a red Adirondack chair, a barbecue grill, and a wooden treehouse.

1. Perfect stopover, getaway, base to explore the area, or to simply stay in town.

Perfect stopover, getaway, base to explore the area, or to simply stay in town.
Bath
8.0 out of 10, Very good, (31 reviews)
"A charming, quiet, and clean room with separate bathroom close to everything downtown. Felt a bit like staying at my grandparent’s house in a good way - it’s very homey. Dmitri is very nice and communication was thorough and easy!"
United States
Esther
The price is AED 410
AED 651 total
includes taxes & fees
25 Oct - 26 Oct
Perfect stopover, getaway, base to explore the area, or to simply stay in town.
A silver convertible car parked in front of a red house with a garden.

2. 1BR Apt. Walk to everything, Large yard. Treehouse. Sun porch. Fall in Maine!

1BR Apt. Walk to everything, Large yard. Treehouse. Sun porch. Fall in Maine!
Bath
8.2 out of 10, Very good, (21 reviews)
"Cute but aging small space, Near attractions"
United States
michael
The price is AED 454
AED 699 total
includes taxes & fees
28 Oct - 29 Oct
1BR Apt. Walk to everything, Large yard. Treehouse. Sun porch. Fall in Maine!
A spacious living room with large windows, a sofa, a chair, and a small table.

3. 1 Mi to Maine Street! MCM-Style Home in Brunswick

1 Mi to Maine Street! MCM-Style Home in Brunswick
Brunswick
9.6 out of 10, Exceptional, (13 reviews)
"Quiet, clean, well appointed house close to Maine St Brunswick and convenient to both Portland and points north. "
United States
Kendra G.
1 Mi to Maine Street! MCM-Style Home in Brunswick
A compact kitchen with a dishwasher, microwave, and coffee maker on the countertop.

4. Quiet Spot in lovely Freeport neighborhood

Quiet Spot in lovely Freeport neighborhood
Freeport
Quiet Spot in lovely Freeport neighborhood
A cozy living room with a wooden ceiling, a sofa, a table, and a sliding glass door leading to a balcony.

5. Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.2 out of 10, Wonderful, (12 reviews)
"The location and views from the cottage are quintessential coastal Maine. Small community with lobster pound and Maine Oyster Company across the street. John is a welcoming host and eager to make sure you enjoy your stay. The cottage is great for 2 people, equipped with the basics and has a great deck to enjoy the views. Planning to return next year. Great spot!"
United States
Rebecca
Mid Coast Getaway w/ water views
A rocking chair and a small table with a decorative plate, both placed on a wooden deck in front of a red building with a white door.

6. 2BR Apt. Authenticic value, Walk to everything, Large yard, Treehouse. No fees.

2BR Apt. Authenticic value, Walk to everything, Large yard, Treehouse. No fees.
Bath
8.8 out of 10, Excellent, (29 reviews)
"Nice place for the money spent"
United States
Kevin P.
The price is AED 760
AED 941 total
includes taxes & fees
28 Oct - 29 Oct
2BR Apt. Authenticic value, Walk to everything, Large yard, Treehouse. No fees.
A modern kitchen with dark cabinetry, a stainless steel range, and a window with a view of greenery.

7. Award Winning Luxury Carriage House a short stroll from town!

Award Winning Luxury Carriage House a short stroll from town!
Bath
10.0 out of 10, Exceptional, (14 reviews)
"Another great stay by a great host. The host Jared even provided some activities for our granddaughters to do while we were on vacation. You will not be disappointed with this property. Looking to stay there again in the future. Thank you, Jared!"
United States
Ronald H.
Award Winning Luxury Carriage House a short stroll from town!
A spacious room with a wooden floor, a dining area with chairs and a table, a sofa, a TV, and a balcony with a view of the sea.

8. 2 bedroom w/ expansive water views

2 bedroom w/ expansive water views
West Point
9.8 out of 10, Exceptional, (7 reviews)
"Place was clean, beautiful and the photos do not do it justice. The perfect get away vacation from the rat race."
United States
Gregory M.
The price is AED 463
AED 884 total
includes taxes & fees
1 Nov - 2 Nov
2 bedroom w/ expansive water views
A wooden cabin with a porch, a rocking chair, and a table with a lantern.

9. Naughty Dog Private Island Log Cabin

Naughty Dog Private Island Log Cabin
Monmouth
10.0 out of 10, Exceptional, (13 reviews)
"Honestly, this property and the whole experience exceeded all my expectations (which were already pretty high). Kent and the team were so accommodating, making sure that we had everything that we needed and were available at any time. They made special plans to accommodate some friends for a day visit and were so kind and helpful. The property itself was so perfect for what we wanted and the dog so enjoyed the freedom that only a private island can bring! Thanks, Kent, for a very memorable stay....
United States
Peter O.
The price is AED 342
AED 1,297 total
includes taxes & fees
3 Nov - 4 Nov
Naughty Dog Private Island Log Cabin
A wooden deck with a view of a lake and trees.

10. 1920s Riverfront Cottage – Historic Maine Charm

1920s Riverfront Cottage – Historic Maine Charm
Edgecomb
9.6 out of 10, Exceptional, (4 reviews)
"Beautiful spot. Make sure to use the hot tub!"
United States
Sam D.
The price is AED 705
AED 1,452 total
includes taxes & fees
2 Nov - 3 Nov
1920s Riverfront Cottage – Historic Maine Charm
A grassy area with a picnic table and chairs, a body of water, and two trees in the background.

11. Orchid Harbor, Bailey Island 3BR

Orchid Harbor, Bailey Island 3BR
Harpswell
10.0 out of 10, Exceptional, (13 reviews)
"Lovely property, close to what we needed and wanted, host communicated promptly. Would definitely stay there again."
United States
Jane D.
Orchid Harbor, Bailey Island 3BR
A spacious living room with a wooden floor, a white sofa, a coffee table, and a dining area with a white table and chairs.

12. Beautiful 3BR Home with Office in Town of Brunswick with King beds

Beautiful 3BR Home with Office in Town of Brunswick with King beds
Brunswick
9.2 out of 10, Wonderful, (7 reviews)
"Great place for our family to stay while visiting the Maine coast."
United States
Craig C.
Beautiful 3BR Home with Office in Town of Brunswick with King beds
A lakeside property with a deck, picnic table, and barbecue grill.

13. Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (72 reviews)
"We had a really nice day in communication and check-in were very easy. Overall, it was a lovely day and we would definitely consider returning."
United States
Len B.
The price is AED 771
AED 1,345 total
includes taxes & fees
1 Nov - 2 Nov
Camp Forever cottage
A wooden deck with a view of a lake, a small building, and surrounding trees.

14. Joyful Maine Escape: A Three-Bedroom Water View Townhouse

Joyful Maine Escape: A Three-Bedroom Water View Townhouse
Edgecomb
10.0 out of 10, Exceptional, (56 reviews)
"This was a very nice home. Clean, comfortable, and lovely. The water views are great, too."
United States
kathleen m.
The price is AED 790
AED 1,546 total
includes taxes & fees
2 Nov - 3 Nov
Joyful Maine Escape: A Three-Bedroom Water View Townhouse
A deck with white railings overlooking a body of water, boats, and a forested shoreline.

15. Captains Watch: A Coastal Escape

Captains Watch: A Coastal Escape
West Point
The price is AED 606
AED 686 total
includes taxes & fees
31 Oct - 1 Nov
Captains Watch: A Coastal Escape
A covered porch with a view of a lake and trees.

16. Mere Point Sunrise Views at Eastern Shore!

Mere Point Sunrise Views at Eastern Shore!
Brunswick
9.8 out of 10, Exceptional, (10 reviews)
"Lovely location "
United States
Michelle S.
The price is AED 580
AED 1,499 total
includes taxes & fees
22 Nov - 23 Nov
Mere Point Sunrise Views at Eastern Shore!
A wooden interior with a radial wooden ceiling design and a central skylight.

17. Island Tree House Glamping

Island Tree House Glamping
Monmouth
10.0 out of 10, Exceptional, (11 reviews)
"Sunset/rise were so perfect, and we got a special appearance of a double rainbow during our stay!"
United States
Desiree L.
The price is AED 103
AED 893 total
includes taxes & fees
29 Oct - 30 Oct
Island Tree House Glamping
A spacious bedroom with a large bed, a rocking chair, and a view of a balcony with a white railing.

18. Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.6 out of 10, Exceptional, (21 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
The price is AED 579
AED 659 total
includes taxes & fees
24 Nov - 25 Nov
Fantastic Waterfront Views
A bedroom with a bed, a small table with a yellow mug, and a window with a view of a forest.

19. Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC

Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC
Georgetown
10.0 out of 10, Exceptional, (2 reviews)
"Really lovely cabin with all the amenities within a stone’s throw to amazing trails and beaches. Would love to come back!"
United States
Palmer M.
The price is AED 774
AED 1,472 total
includes taxes & fees
4 Nov - 5 Nov
Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC
A living room with a sofa, armchair, wooden coffee table, and a potted plant.

20. Fully Updated Airy Historic Home in South Freeport

Fully Updated Airy Historic Home in South Freeport
Freeport
10.0 out of 10, Exceptional, (1 review)
"Great property well kept and close to everything we wanted to do"
United States
boodu
Fully Updated Airy Historic Home in South Freeport
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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Top Woolwich Hotel Reviews

The Federal

The Federal

10/10 Excellent
"Very lovely property close to downtown and close to campus, but our room was a bit small. No dresser or drawer space. Restaurant was great, but no breakfast options."
Karen 3-night trip
Posted 12 hours ago
The Federal