Search Cottages in Chamberlain

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov

Featured Cottages in Chamberlain and around

Boothbay Harbor Cottage Overlooking Mill Cove
Marina

Boothbay Harbor Cottage Overlooking Mill Cove

9.8 out of 10, Exceptional, (22)
"Clean, close to downtown."
Boothbay Harbor Cottage Overlooking Mill Cove
Premier Cottage, #3, w/NEW ADDITION! Now Sleeps 8, Pets Free
Beach

Premier Cottage, #3, w/NEW ADDITION! Now Sleeps 8, Pets Free

10.0 out of 10, Exceptional, (48)
"Loved it on every level. Cottage was super clean and loved the style and the size. There is a pond and a field out back with fireplaces and areas to sit and hang out. Perfect for the morning walk with the dog. The cottages are fairly close to each other but each had their own very private deck so I didn’t mind at all. Communication from the hosts was also perfect whilst leaving you enough privacy. Would come back for sure. "
Premier Cottage, #3, w/NEW ADDITION! Now Sleeps 8, Pets Free
Peaceful, Oceanfront Retreat, Sleeps 8, Semi-Private Sandy Swim Area
Property grounds

Peaceful, Oceanfront Retreat, Sleeps 8, Semi-Private Sandy Swim Area

10.0 out of 10, Exceptional, (47)
"Beautiful property & so clean & well appointed, great location! Had everything we wanted for a wonderful vacation week!"
Peaceful, Oceanfront Retreat, Sleeps 8, Semi-Private Sandy Swim Area
Modern woodland privacy with ocean, trails, and lobster all in walking distance.
Outdoor dining

Modern woodland privacy with ocean, trails, and lobster all in walking distance.

10.0 out of 10, Exceptional, (48)
"My friend and I felt very relaxed at this house. The beds were comfortable and the kitchen was stocked with most every cooking equipment needed. The host answered any question I had very quickly and supplied information about the surrounding area. It was a great place to unwind!"
Modern woodland privacy with ocean, trails, and lobster all in walking distance.
Gorgeous Waterfront Home on Westport Island with 2 Sunrooms
TV

Gorgeous Waterfront Home on Westport Island with 2 Sunrooms

9.4 out of 10, Exceptional, (51)
"This home is so wonderful to stay in. My sister and I find this to be the perfect place to meet each other and relax with our family. Beautiful space. "
Gorgeous Waterfront Home on Westport Island with 2 Sunrooms
Happy Cottage Near Everything 11
Outdoor dining

Happy Cottage Near Everything 11

8.0 out of 10, Very good, (1)
"Very comfortable, clean small cottage. We slept great in the bed that was provided and it had a futon in the living area . We recommend that only 2 people stay there. They had a toaster oven , a full refrigerator and a coffee maker. It is very close to Route 1, Boothbay Harbor and Damariscotta. "
Happy Cottage Near Everything 11
Dog-friendly, bayfront home - gorgeous ocean views, private balcony & fireplace
TV, fireplace, DVD player, books

Dog-friendly, bayfront home - gorgeous ocean views, private balcony & fireplace

9.2 out of 10, Wonderful, (68)
"Wonderful views."
Dog-friendly, bayfront home - gorgeous ocean views, private balcony & fireplace
‘Paul’s Cottage’ in Tenants Harbor, 1 Min to Shore
Terrace/patio

‘Paul’s Cottage’ in Tenants Harbor, 1 Min to Shore

9.6 out of 10, Exceptional, (44)
"Tenants Harbor 🎉"
‘Paul’s Cottage’ in Tenants Harbor, 1 Min to Shore
Updated lake cottage right on Damariscotta Lake.
Property grounds

Updated lake cottage right on Damariscotta Lake.

10.0 out of 10, Exceptional, (144)
"Best location on lake. House was warm and recently updated. Fun time "
Updated lake cottage right on Damariscotta Lake.
Spacious 1 Bedroom Close to Everything 4
Marina

Spacious 1 Bedroom Close to Everything 4

9.8 out of 10, Exceptional, (19)
"This was a lovely little cabin. Everything was as described and my husband and I really enjoyed our stay."
Spacious 1 Bedroom Close to Everything 4
Dreamy Wooded Cabin W/ Spacious Deck, Free WiFi, Secluded Location & More
Terrace/patio

Dreamy Wooded Cabin W/ Spacious Deck, Free WiFi, Secluded Location & More

9.6 out of 10, Exceptional, (24)
"Very nice all the basics covered. Close to the harbor, very quiet."
Dreamy Wooded Cabin W/ Spacious Deck, Free WiFi, Secluded Location & More
Lilac Cottage - Near Georgetown Island - Midcoast Maine
Interior

Lilac Cottage - Near Georgetown Island - Midcoast Maine

10.0 out of 10, Exceptional, (24)
"We had a wonderful stay at this property. Our dogs loved being able to chase eachother around the yard"
Lilac Cottage - Near Georgetown Island - Midcoast Maine
Your own private island! Rustic and close to Nature.
Dining

Your own private island! Rustic and close to Nature.

9.4 out of 10, Exceptional, (33)
"wonderful place, glamping, wildlife all around, you can't but enjoy the beauty of Mid Coast Maine. Thanks for sharing your island with all of us !"
Your own private island! Rustic and close to Nature.
Enjoyable 1-bedroom rustic cottage in Southport.
Terrace/patio

Enjoyable 1-bedroom rustic cottage in Southport.

10.0 out of 10, Exceptional, (11)
Enjoyable 1-bedroom rustic cottage in Southport.
Waterfront Cottage in South Bristol w/ private dock and lobster boat views
Exterior

Waterfront Cottage in South Bristol w/ private dock and lobster boat views

10.0 out of 10, Exceptional, (106)
"We stayed at the property for two nights for a family getaway after the holidays. The house was in a great location, beautiful views, spotlessly clean, and very well equipped. We loved waking up to the light hitting the water and being able to explore the beautiful peninsula. Great hikes a short drive away. We would gladly stay again! "
Waterfront Cottage in South Bristol w/ private dock and lobster boat views
Charming Cottage with Ocean Views, Wifi, and Washer and Dryer
Fridge, microwave, oven, stovetop

Charming Cottage with Ocean Views, Wifi, and Washer and Dryer

10.0 out of 10, Exceptional, (1)
"We had the best week at Sea Breeze in our first trip to Maine! After a long drive, we were stunned to turn the corner to find our home overlooking a gorgeous seaside, situated on a quiet, walkable, friendly street. When we stepped inside, we found the house to be a clean, cozy, and quiet haven that had plenty of space to relax, play board games, and enjoy family breakfasts around the table. There was ample space in the fridge and freezer for all of our locally-purchased groceries, the kitchen...
Charming Cottage with Ocean Views, Wifi, and Washer and Dryer
Amazing All-Season Sprucewold Cabin w/ Private Beach Club Access
Terrace/patio

Amazing All-Season Sprucewold Cabin w/ Private Beach Club Access

9.6 out of 10, Exceptional, (69)
"Great spot"
Amazing All-Season Sprucewold Cabin w/ Private Beach Club Access
Olde Post Office Cottage at Pemaquid Point
Fitness facility

Olde Post Office Cottage at Pemaquid Point

9.6 out of 10, Exceptional, (140)
"This is our second time staying here, and as before, it was delightful. Obvious that the owner puts a lot of care and thought into the place."
Olde Post Office Cottage at Pemaquid Point
' The Castle House' of Rutherfords Island, Christmas Cove
3 bedrooms, iron/ironing board, travel cot, WiFi

' The Castle House' of Rutherfords Island, Christmas Cove

10.0 out of 10, Exceptional, (13)
"Great location and amenities available."
' The Castle House' of Rutherfords Island, Christmas Cove
Renovated home with water views, dock access, - dogs okay
Fridge, microwave, oven, stovetop

Renovated home with water views, dock access, - dogs okay

6.6 out of 10, (8)
"location was great. bed sheets/ covers were not clean. nice kitchen no outside chairs or deck to enjoy the Maine weather."
Renovated home with water views, dock access, - dogs okay
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chamberlain Hotel Reviews

Tugboat Inn

Tugboat Inn

10/10 Excellent
"We went last minute and it was one of the last available rooms. Its beautiful and amazingly beautiful views. I actually do noz think anywhere along that area would be disappointing. Loving New England is loving the ins ans outs of the coast walk to amazing dinner or lobster roll lunch .iysters everywhere ...I live inland and Booth bay is Heaven revisited."
Joy 1-night trip
Posted 17 hours ago
Tugboat Inn

Frequently asked questions

How much do cottages in Chamberlain cost?
Cottages in Chamberlain range between and per night. These retreats offer a chance to get reacquainted with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Chamberlain?
There are 225 cottages in Chamberlain. Whether you're travelling with the family or planning a retreat with your friends, Expedia will help you find the ideal space to reconnect with nature.
Are there any family-friendly cottages in Chamberlain?
Spend your family holiday at Pine Cliff Dweller Southport - 2 Bedroom Cottage, a 2.5-star cottage not far from town. Conveniences here include a fireplace and WiFi. Another family-friendly option where you can swap the urban jungle for wide open spaces is Piffi Biff Southport - 5 Bedroom Cottage. A barbecue grill and a fireplace help make this 2-star cottage a top pick. Chamberlain has no shortage of family-friendly attractions to check out that'll keep the kids entertained. Boothbay Railway Village and Boothbay Railway Village promise a fun-filled day for all ages.