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Chamberlain Vacation Rentals

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Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Chamberlain vacation rentals

Outdoor dining

1. Applecroft Cabin No. 3 - Modern off-grid cabin deep in the woods.

Applecroft Cabin No. 3 - Modern off-grid cabin deep in the woods.
Waldoboro
$194 nightly
The price is $212
Sep 1 - Sep 2
Total with taxes and fees
Applecroft Cabin No. 3 - Modern off-grid cabin deep in the woods.
Terrace/patio

2. Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything

Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
Boothbay
7.8 out of 10, Good, (10 reviews)
"Great stay! Pet friendly, super responsive host and excellent location!"
United States
Cassie M.
$150 nightly
The price is $163
Aug 12 - Aug 13
Total with taxes and fees
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
Outdoor dining

3. Happy Cottage Near Everything 11

Happy Cottage Near Everything 11
Edgecomb
6.8 out of 10, (3 reviews)
"Great quit little place, great accommodations with even better help and information about the local area."
United States
George
$239 nightly
The price is $242
Aug 19 - Aug 20
Total with taxes and fees
Happy Cottage Near Everything 11
Coffee/tea maker, fridge, microwave, stovetop

4. Spacious 1 Bedroom Cottage Close to Everything 5

Spacious 1 Bedroom Cottage Close to Everything 5
Edgecomb
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful, clean, small cottage close to the coast, shopping and dining."
United States
Theresa
$264 nightly
The price is $279
Aug 18 - Aug 19
Total with taxes and fees
Spacious 1 Bedroom Cottage Close to Everything 5
Coffee/tea maker, fridge, microwave, oven

5. Shipbuilder's Retreat, Unit 2, Sleeps 6, 5 minutes to Harbor

Shipbuilder's Retreat, Unit 2, Sleeps 6, 5 minutes to Harbor
East Boothbay
10.0 out of 10, Exceptional, (32 reviews)
"Close enough to BoothBay Harbour and Botanical Gardens but private and quiet get away. Very comfortable! Spacious, good appliances and bedding. I would guess very new. Loved it!"
United States
Judith
$503 nightly
The price is $548
Sep 6 - Sep 7
Total with taxes and fees
Shipbuilder's Retreat, Unit 2, Sleeps 6, 5 minutes to Harbor
Property grounds

6. Newly renovated motel garden rooms heart of boothbay affordable great hospitaliy

Newly renovated motel garden rooms heart of boothbay affordable great hospitaliy
Boothbay
6.0 out of 10, (5 reviews)
"It had a very homey feel, was nice to stay at for the night and wasn’t far from town."
United States
Audreyana P.
$189 nightly
The price is $206
Sep 1 - Sep 2
Total with taxes and fees
Newly renovated motel garden rooms heart of boothbay affordable great hospitaliy
Terrace/patio

7. Newly Renovated Cozy Cove Cabin at White Anchor Inn

Newly Renovated Cozy Cove Cabin at White Anchor Inn
Boothbay
8.6 out of 10, Excellent, (8 reviews)
"As advertised, comfy bed cozy cabin. Would stay again "
United States
Joseph B.
$205 nightly
The price is $223
Aug 18 - Aug 19
Total with taxes and fees
Newly Renovated Cozy Cove Cabin at White Anchor Inn
2 bedrooms, iron/ironing board, bed sheets

8. Cheerful Cottage with Loft 9

Cheerful Cottage with Loft 9
Edgecomb
10.0 out of 10, Exceptional, (4 reviews)
"Immaculate, very cute - “tiny cottage”We loved it!"
United States
Daniel B.
$256 nightly
The price is $270
Sep 8 - Sep 9
Total with taxes and fees
Cheerful Cottage with Loft 9
Terrace/patio

9. Renovated The Driftwood Cabin at White Anchor Inn

Renovated The Driftwood Cabin at White Anchor Inn
Boothbay
8.8 out of 10, Excellent, (3 reviews)
"Communication with Property Owner was excellent. This cute little cottage has been renovated and has a nice feel indoors. There is a beautiful porch on the back with a lovely view. The unit includes a mini fridge and mini microwave along with a little table and two chairs. If you have long hair, water pressure could be a concern. My shower worked great but the sink water pressure was not strong. The bed was comfortable and the decor was nice. The air conditioning works fine."
United States
Abra H.
$222 nightly
The price is $242
Aug 18 - Aug 19
Total with taxes and fees
Renovated The Driftwood Cabin at White Anchor Inn
Coffee/tea maker, fridge, microwave, oven

10. Shipbuilder’s Retreat sleeps 6, 5 minutes to Harbor

Shipbuilder’s Retreat sleeps 6, 5 minutes to Harbor
East Boothbay
10.0 out of 10, Exceptional, (56 reviews)
"Excellent, clean property. "
United States
Andy H.
$563 nightly
The price is $613
Aug 16 - Aug 17
Total with taxes and fees
Shipbuilder’s Retreat sleeps 6, 5 minutes to Harbor
Exterior

11. Spacious 1 Bedroom Cottage Close to Everything 3

Spacious 1 Bedroom Cottage Close to Everything 3
Edgecomb
9.8 out of 10, Exceptional, (17 reviews)
"Great central location"
United States
Bruce O.
$289 nightly
The price is $306
Sep 8 - Sep 9
Total with taxes and fees
Spacious 1 Bedroom Cottage Close to Everything 3
Smart TV, DVD player, books, video library

12. A Spacious Vacation Cottage in Sheepscot Harbour

A Spacious Vacation Cottage in Sheepscot Harbour
Edgecomb
10.0 out of 10, Exceptional, (67 reviews)
"Great place and great restaurants."
United States
Julie D.
$319 nightly
The price is $348
Aug 17 - Aug 18
Total with taxes and fees
A Spacious Vacation Cottage in Sheepscot Harbour
House (3 Bedrooms) | Front of property

13. Near Lakes, Bay & Trails! Historic Waldoboro Gem

Near Lakes, Bay & Trails! Historic Waldoboro Gem
3.0 star property
Waldoboro
10.0 out of 10, Exceptional, (2 reviews)
"This home is such a gem! A historic home that is updated with many modern conveniences. We’ve been to MANY AirB&B’s and this home was probably the best equipped we’ve been in! Convenient to Boothbay and lots of downeast inlets and harbors. Very quiet, but close to groceries, food and farm stands. Our only regret was not staying longer- we would have loved to grill and use the fire pit!"
United States
Deborah
$450 nightly
The price is $491
Aug 14 - Aug 15
Total with taxes and fees
Near Lakes, Bay & Trails! Historic Waldoboro Gem
Coffee/tea maker, fridge, microwave, stovetop

14. Near Lakes, Bay & Trails! Historic Waldoboro Gem

Near Lakes, Bay & Trails! Historic Waldoboro Gem
Waldoboro
9.8 out of 10, Exceptional, (27 reviews)
"It was a wonderful stay at this home. The home was incredibly clean, the beds were very comfortable and had great bedding on them. It was a great location to all the nearby places we wanted to go to. Loved the historic charm. We would love to come and stay again!"
United States
Tina S.
$461 nightly
The price is $502
Aug 14 - Aug 15
Total with taxes and fees
Near Lakes, Bay & Trails! Historic Waldoboro Gem
Outdoor dining

15. Captain's Guest Room. Authenticity. Great Value. Walk to everything.

Captain's Guest Room. Authenticity. Great Value. Walk to everything.
Bath
8.4 out of 10, Very Good, (27 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
$165 nightly
The price is $180
Aug 30 - Aug 31
Total with taxes and fees
Captain's Guest Room. Authenticity. Great Value. Walk to everything.
Property grounds

16. Spectacular Waterfront Cottage: Charming Getaway on The Sheepscot River

Spectacular Waterfront Cottage: Charming Getaway on The Sheepscot River
Edgecomb
9.8 out of 10, Exceptional, (86 reviews)
"The cottage was perfect for our stay. The location is great for visiting all the sights, shopping, and dining in the area. But, we could have just stayed at the cottage, relaxed, and Bern perfectly happy. "
United States
Ann M.
$372 nightly
The price is $405
Aug 13 - Aug 14
Total with taxes and fees
Spectacular Waterfront Cottage: Charming Getaway on The Sheepscot River
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 Chamberlain Hotel Reviews

Topside Inn

Topside Inn

10/10 Excellent
"Excellent gourmet breakfast every morning."
Gregory 6-night trip
Posted 13 hours ago
Topside Inn

Find out more about Chamberlain

Everything you need to know about Chamberlain vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chamberlain vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chamberlain vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chamberlain vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chamberlain. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chamberlain in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $163 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chamberlain rentals

At Expedia, we put the best Chamberlain vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chamberlain rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chamberlain vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chamberlain. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Chamberlain?

Yes, you can find vacation rentals close to the most popular points of interest in Chamberlain, or you can go with a more secluded option if you're looking for relaxation.

What are some of the best vacation home rentals that Chamberlain has to offer?

Captain's 2BR Suite. Best value, near everything, big yard, treehouse. No fees. : Visitors like this Chamberlain vacation home rental. It offers a patio, a garden, and WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave, and a coffee maker.

What’s there to see and do in Chamberlain?

While exploring the area, visit family-friendly sights like Boothbay Railway Village, or get outside and enjoy nature at Rachel Carson Salt Pond Preserve. Pemaquid Beach Park and Pemaquid Point Lighthouse Park are a couple of places you'll find in the larger area.

What’s a vacation rental in Chamberlain like?

Vacation rentals are private properties you can stay in for short or long periods in Chamberlain. Vacation rentals offer amenities such as WiFi and washers and dryers so you'll feel right at home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of safety away from shared hotel elevators and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for family trips or small group gatherings.