Search Vacation Homes in Woolwich

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Our top choices for Woolwich vacation homes

Property grounds
Cozy Cottage on water's edge of Lake Cobbosseecontee

Cozy Cottage on water's edge of Lake Cobbosseecontee

Manchester
8.6 out of 10, Excellent, (18)
"Great views of the from the screened porch! Lots to loons too, a big bonus!"
United States
Randy P.
The price is AED 479
AED 1,171 total
includes taxes & fees
10 Dec - 11 Dec
Cozy Cottage on water's edge of Lake Cobbosseecontee
Dining
Escape to Positive Outlook

Escape to Positive Outlook

West Point
10.0 out of 10, Exceptional, (2)
"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 347
AED 742 total
includes taxes & fees
10 Dec - 11 Dec
Escape to Positive Outlook
Property grounds
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

Nobleboro
9.8 out of 10, Exceptional, (43)
"House was very clean and beautiful the beach and fishing are were lovely as well very nicecstay"
United States
Lori R.
The price is AED 493
AED 1,073 total
includes taxes & fees
10 Dec - 11 Dec
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
Terrace/patio
Laughton House @ Pemaquid Beach

Laughton House @ Pemaquid Beach

Pemaquid Beach
10.0 out of 10, Exceptional, (8)
"This house is in a great location. We could walk to the beach, or to Fort Henry to let my grandsons run around. The house is lovely and had everything we needed. We have come to this area of Maine since 2017, and this had been our favorite place to stay! "
United States
Dawn W.
The price is AED 892
AED 2,006 total
includes taxes & fees
13 Dec - 14 Dec
Laughton House @ Pemaquid Beach
Fridge, microwave, stovetop, coffee/tea maker
The Outlet Studio, Rustic Comfort w Fireplace

The Outlet Studio, Rustic Comfort w Fireplace

Freeport
10.0 out of 10, Exceptional, (11)
"Very comfortable, clean, with a spacious bathroom and within walking distance of downtown Freeport and Bow Street Market"
United States
Deanna S.
The price is AED 298
AED 585 total
includes taxes & fees
10 Dec - 11 Dec
The Outlet Studio, Rustic Comfort w Fireplace
3 bedrooms, WiFi
Fantastic Waterfront Views

Fantastic Waterfront Views

West Point
9.6 out of 10, Exceptional, (14)
"Our favorite part about our stay at this location was being able to look out the many sliding door windows to see the ocean view. It was a very relaxing place to stay. "
United States
Heather S.
The price is AED 771
AED 1,380 total
includes taxes & fees
6 Jan - 7 January 2026
Fantastic Waterfront Views
Outdoor dining
Camp Forever cottage

Camp Forever cottage

Harpswell
9.6 out of 10, Exceptional, (58)
"Most enjoyed vacation this year.Location was beautiful. "
United States
Debra S.
The price is AED 771
AED 1,333 total
includes taxes & fees
31 Dec - 1 January 2026
Camp Forever cottage
Fridge, microwave, oven, stovetop
Private Home w/ Office Year Round in town Brunswick next to Bowdoin

Private Home w/ Office Year Round in town Brunswick next to Bowdoin

Brunswick
8.8 out of 10, Excellent, (23)
"Nice place, I'd stay again!"
United States
Ronnie C.
The price is AED 496
AED 1,401 total
includes taxes & fees
10 Dec - 11 Dec
Private Home w/ Office Year Round in town Brunswick next to Bowdoin
Outdoor dining
Maine Coast House with Spectacular Ocean Views and Beach for Swimming

Maine Coast House with Spectacular Ocean Views and Beach for Swimming

South Bristol
9.4 out of 10, Exceptional, (27)
"Perfect base for exploring the mid-coast region. "
United States
Rebecca M.
The price is AED 708
AED 1,777 total
includes taxes & fees
14 Dec - 15 Dec
Maine Coast House with Spectacular Ocean Views and Beach for Swimming
Paper towels
Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard

Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard

2.0 star property
Brunswick
The price is AED 606
AED 1,649 total
includes taxes & fees
6 Jan - 7 January 2026
Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard
Fridge, microwave, oven, stovetop
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, (5)
"Great place for our family to stay while visiting the Maine coast."
United States
Craig C.
The price is AED 514
AED 1,305 total
includes taxes & fees
21 Dec - 22 Dec
Beautiful 3BR Home with Office in Town of Brunswick with King beds
Beach
Pemaquid Escape | Curated Comfort + Hot Tub

Pemaquid Escape | Curated Comfort + Hot Tub

Walpole
10.0 out of 10, Exceptional, (2)
"This was a last minute booking for our family as we had a basketball tournament, there were 8 of us including 3 children. This was the most kid friendly house we have stayed in! It was so well stocked for the entire family. The house was meticulously cleaned and the hosts were very responsive to any questions! "
United States
Melissa L.
The price is AED 1,091
AED 2,502 total
includes taxes & fees
10 Dec - 11 Dec
Pemaquid Escape | Curated Comfort + Hot Tub
Fridge, microwave, oven, stovetop
Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport

Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport

Freeport
10.0 out of 10, Exceptional, (4)
"We had a wonderful time in Freeport, getting some Christmas season shopping in and bring our 4 year old to the Sparkle weekend festivities. "
United States
David H.
The price is AED 901
AED 2,522 total
includes taxes & fees
15 Dec - 16 Dec
Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport
Interior
Spacious Country Home Freeport, Only 5 min to LL Bean!

Spacious Country Home Freeport, Only 5 min to LL Bean!

Freeport
9.6 out of 10, Exceptional, (15)
"It was a very relaxing house to stay in. Everything was provided in the kitchen, bathroom and bedrooms. Lots of room for all of us to mingle. "
United States
Carla S.
The price is AED 639
AED 1,824 total
includes taxes & fees
10 Dec - 11 Dec
Spacious Country Home Freeport, Only 5 min to LL Bean!
Fridge, microwave, oven, stovetop
Generous Living in a Warm, Welcoming Home

Generous Living in a Warm, Welcoming Home

Topsham
The price is AED 546
AED 1,800 total
includes taxes & fees
10 Dec - 11 Dec
Generous Living in a Warm, Welcoming Home
Private kitchen
Classic New England Waterfront

Classic New England Waterfront

Harpswell
10.0 out of 10, Exceptional, (2)
"Great property"
United States
Scott D.
The price is AED 918
AED 2,606 total
includes taxes & fees
10 Dec - 11 Dec
Classic New England Waterfront
Fridge, microwave, oven, stovetop
Maine Luxury Home On the Sea

Maine Luxury Home On the Sea

Brunswick
The price is AED 1,037
AED 2,892 total
includes taxes & fees
10 Dec - 11 Dec
Maine Luxury Home On the Sea
Smart TV, books
Ambleside in Boothbay Harbor Maine! Perfect for a warm and cozy Gardens Aglow!

Ambleside in Boothbay Harbor Maine! Perfect for a warm and cozy Gardens Aglow!

Boothbay Harbor
10.0 out of 10, Exceptional, (7)
"The property is beautiful and within walking distance to the main town area. The house has plenty of space for my family of 10 and the host went above and beyond with amenities."
United States
Leang C.
The price is AED 2,387
AED 3,203 total
includes taxes & fees
10 Dec - 11 Dec
Ambleside in Boothbay Harbor Maine! Perfect for a warm and cozy Gardens Aglow!
Fridge, microwave, oven, stovetop
Award Winning Luxury Carriage House a short stroll from town!

Award Winning Luxury Carriage House a short stroll from town!

2.0 star property
Bath
10.0 out of 10, Exceptional, (9)
"An exceptional property and guest. Would love to stay again next time Thank you Jared and Heather!"
United States
Ronald H.
The price is AED 1,561
AED 2,378 total
includes taxes & fees
11 Dec - 12 Dec
Award Winning Luxury Carriage House a short stroll from town!
Interior
Camp Lintonia on Tacoma Lakes

Camp Lintonia on Tacoma Lakes

Litchfield
10.0 out of 10, Exceptional, (11)
"Booked this property for a girls trip and this property was stunning! Wish we would’ve booked for more days! Ample space for everyone, views were amazing, and the house was gorgeous! Already considering booking again next year! "
United States
Emma B.
The price is AED 1,818
AED 2,266 total
includes taxes & fees
10 Dec - 11 Dec
Camp Lintonia on Tacoma Lakes
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Woolwich Hotel Reviews

The Federal

The Federal

10/10 Excellent
"It was a joy to stay in a "non-big box" hotel: the room was cozy, the bed was comfortable, the whole space was beautiful, and the whole vibe was wonderful. Delicious coffee was available in the hallway on each floor starting at 6 am--even better! We hope to stay here again!"
Rebecca 1-night trip
Posted 1 day ago
The Federal