Default HTG hotel image

Chamberlain Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Chamberlain vacation rentals

1. 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
The price is CA $345
CA $769 total
includes taxes & fees
Sep 13 - Sep 14
Shipbuilder's Retreat, Unit 2, Sleeps 6, 5 minutes to Harbor

2. 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.
The price is CA $406
CA $848 total
includes taxes & fees
Aug 16 - Aug 17
Shipbuilder’s Retreat sleeps 6, 5 minutes to Harbor

3. Fully Renovated "Saltbox" Home in Boothbay

Fully Renovated "Saltbox" Home in Boothbay
Boothbay
The price is CA $505
CA $1,069 total
includes taxes & fees
Aug 20 - Aug 21
Fully Renovated "Saltbox" Home in Boothbay

4. 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.
The price is CA $187
CA $281 total
includes taxes & fees
Sep 1 - Sep 2
Newly renovated motel garden rooms heart of boothbay affordable great hospitaliy

5. 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.
The price is CA $186
CA $280 total
includes taxes & fees
Aug 16 - Aug 17
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything

6. Walk-to-Town Boothbay Harbor Retreat | Harbor Views | A/C | Parking| Pet Friendly

Walk-to-Town Boothbay Harbor Retreat | Harbor Views | A/C | Parking| Pet Friendly
Boothbay Harbor
6.0 out of 10, (1 review)
"Ok Beautiful location price was on the high side but very clean and state of the art."
United States
Steve R.
The price is CA $609
CA $1,225 total
includes taxes & fees
Aug 29 - Aug 30
Walk-to-Town Boothbay Harbor Retreat | Harbor Views | A/C | Parking| Pet Friendly

7. Boothbay Harbor, 2-Story Cottage, downtown

Boothbay Harbor, 2-Story Cottage, downtown
Boothbay Harbor
9.4 out of 10, Exceptional, (29 reviews)
"Enjoyed the place, great location. "
United States
Erik P.
The price is CA $333
CA $584 total
includes taxes & fees
Aug 17 - Aug 18
Boothbay Harbor, 2-Story Cottage, downtown

8. Boothbay Harbor, The Francis Greene House, downtown

Boothbay Harbor, The Francis Greene House, downtown
Boothbay Harbor
9.4 out of 10, Exceptional, (48 reviews)
"We spent three nights at this location, which is just a short walk from the commercial area of Boothbay Harbor. In addition to restaurants in town it is only minutes away from Robinson's Wharf, which had some of the best food we experienced in 14 days of travel - definitely the best lobster. The house was as advertised and suited our needs well."
United States
Terry F.
The price is CA $527
CA $1,000 total
includes taxes & fees
Sep 10 - Sep 11
Boothbay Harbor, The Francis Greene House, downtown

9. Harold Room 8 | 2 Queens + Gable Windows

Harold Room 8 | 2 Queens + Gable Windows
Boothbay Harbor
The price is CA $527
CA $662 total
includes taxes & fees
Aug 30 - Aug 31
Harold Room 8 | 2 Queens + Gable Windows

10. Pelican Cottage | 2 BR + Waterfront Porch

Pelican Cottage | 2 BR + Waterfront Porch
Boothbay Harbor
The price is CA $1,023
CA $1,273 total
includes taxes & fees
Sep 7 - Sep 8
Pelican Cottage | 2 BR + Waterfront Porch

11. Oriole Suite | Stone Fireplace + Woodland

Oriole Suite | Stone Fireplace + Woodland
Boothbay Harbor
The price is CA $874
CA $1,072 total
includes taxes & fees
Aug 31 - Sep 1
Oriole Suite | Stone Fireplace + Woodland

12. Modern Cape -3 Bedroom- Boothbay Harbor - Near Ocean -Golf-Botanical Gardens

Modern Cape -3 Bedroom- Boothbay Harbor - Near Ocean -Golf-Botanical Gardens
Boothbay Harbor
10.0 out of 10, Exceptional, (4 reviews)
"The house was very charming, very clean & perfectly located to trails, botanical gardens, train museum & harbor! The house had everything that you could possibly need & we especially enjoyed the fire pit multiple nights!"
United States
Sharon H.
The price is CA $429
CA $871 total
includes taxes & fees
Sep 2 - Sep 3
Modern Cape -3 Bedroom- Boothbay Harbor - Near Ocean -Golf-Botanical Gardens

13. Classic Maine Waterfront Home on the Back River – Trevett

Classic Maine Waterfront Home on the Back River – Trevett
Boothbay
The price is CA $694
CA $1,296 total
includes taxes & fees
Sep 2 - Sep 3
Classic Maine Waterfront Home on the Back River – Trevett

14. 1920s Riverfront Cottage – Historic Maine Charm

1920s Riverfront Cottage – Historic Maine Charm
Edgecomb
8.0 out of 10, Very good, (1 review)
"This cottage is the perfect blend of historic charm and modern upgrades. The view of the river is incredible, and the secluded location is just a short drive from downtown Wiscasset and Edgecomb. The sunroom is already a great place to hang out and enjoy the river view, but the owners are also putting in a lot of work to create an enjoyable outdoor space. Jeffrey is easy to work with and honestly wants you to have a good stay."
United States
Shelly
The price is CA $323
CA $612 total
includes taxes & fees
Sep 8 - Sep 9
1920s Riverfront Cottage – Historic Maine Charm

15. 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.
The price is CA $221
CA $330 total
includes taxes & fees
Aug 23 - Aug 24
Renovated The Driftwood Cabin at White Anchor Inn

16. 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.
The price is CA $215
CA $315 total
includes taxes & fees
Aug 30 - Aug 31
Newly Renovated Cozy Cove Cabin at White Anchor Inn

17. Luxury Yurt at Seaside Farm in Friendship

Luxury Yurt at Seaside Farm in Friendship
Friendship
The price is CA $402
CA $991 total
includes taxes & fees
Sep 6 - Sep 7
Luxury Yurt at Seaside Farm in Friendship

18. Druce Room 1 | Ocean Deck + French Doors

Druce Room 1 | Ocean Deck + French Doors
Boothbay Harbor
The price is CA $692
CA $859 total
includes taxes & fees
Aug 30 - Aug 31
Druce Room 1 | Ocean Deck + French Doors

19. Crow's Nest | Panoramic Ocean Views - Queen

Crow's Nest | Panoramic Ocean Views - Queen
Boothbay Harbor
The price is CA $692
CA $853 total
includes taxes & fees
Aug 31 - Sep 1
Crow's Nest | Panoramic Ocean Views - Queen

20. Windward Suite | Harbor View + Enclosed Porch

Windward Suite | Harbor View + Enclosed Porch
Boothbay Harbor
The price is CA $857
CA $1,051 total
includes taxes & fees
Aug 31 - Sep 1
Windward Suite | Harbor View + Enclosed Porch
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

Top Chamberlain Hotel Reviews

Find out more about Chamberlain

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Chamberlain. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.