Chamberlain Vacation Rentals

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Vacation Rentals in Chamberlain

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

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

Beautiful Harbor Views Heart of Boothbay Harbor Downtown Village near all Piers

9.6 out of 10, Exceptional, (75)
"We loved our stay here. This is a fantastic location and has everything you need to enjoy your stay in Boothbay. Bring eye masks though, the futon sleeper is going to get a lot of light from the windows."
Beautiful Harbor Views Heart of Boothbay Harbor Downtown Village near all Piers

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

The price is ¥19,287
¥29,561 total
includes taxes & fees
Aug 22 - Aug 23
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything

Captain's Quarters Guest Room w/Private Bath & Entrance. Best Value in Town!

7.4 out of 10, Good, (12)
"Clean, well maintained, slighly funky in an historical way . Very convenient to great breakfast spots and downtown Bath. Would stay there again."
The price is ¥13,301
¥24,164 total
includes taxes & fees
Aug 14 - Aug 15
Captain's Quarters Guest Room w/Private Bath & Entrance. Best Value in Town!

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.

Cozy Cottage with Ocean Views, Sunsets and Dog-Friendly Charm

2.0 star property
9.4 out of 10, Exceptional, (9)
"Beautiful location, peaceful and great views"
Cozy Cottage with Ocean Views, Sunsets and Dog-Friendly Charm

Oceanfront Cottage w/ Deck 2 Mi to Boothbay Harbor

3.0 star property
Oceanfront Cottage w/ Deck 2 Mi to Boothbay Harbor

Oceanfront escape with deck, views of Lobster Cove & firepit - walk to town

9.6 out of 10, Exceptional, (30)
"The cabin was very clean and a nice quiet location. Had everything we needed for a comfortable stay."
Oceanfront escape with deck, views of Lobster Cove & firepit - walk to town

A Charming Waterfront Cottage with Touches of Elegance

10.0 out of 10, Exceptional, (113)
"The house is so lovely and the property very peaceful. It was a great place to celebrate graduation and Mother’s Day The property manager, Mr. Lawrence, was gracious and friendly and a wealth of information!"
A Charming Waterfront Cottage with Touches of Elegance

The Sea Eagle - Luxury 5 BR Waterfront Home in Boothbay Harbor with private dock

10.0 out of 10, Exceptional, (5)
"Loved our stay. Walking distance to everything. Kids loved the kayaks & dock. We loved having coffee on the harbor every morning. Plenty of room for multiple families. "
The Sea Eagle - Luxury 5 BR Waterfront Home in Boothbay Harbor with private dock

Last minute deal Ocean Point OCEANFRONT with private BEACH

10.0 out of 10, Exceptional, (93)
"Everything was perfect!"
Last minute deal Ocean Point OCEANFRONT with private BEACH

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

10.0 out of 10, Exceptional, (27)
"The owners were ver accommodating and the place is a quiet, pretty location "
The price is ¥25,804
¥50,517 total
includes taxes & fees
Aug 26 - Aug 27
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

Newly Renovated Cozy Cove Cabin at White Anchor Inn

10.0 out of 10, Exceptional, (1)
"As advertised, comfy bed cozy cabin. Would stay again "
The price is ¥22,907
¥34,151 total
includes taxes & fees
Aug 31 - Sep 1
Newly Renovated Cozy Cove Cabin at White Anchor Inn

Peaceful Lake Waterfront! Automatic backup Generator! Full Kitchen! Heat & A/C

10.0 out of 10, Exceptional, (100)
"Adorable place, roomy, quiet, upscale yet felt just like home. Will definitely stay again! "
Peaceful Lake Waterfront! Automatic backup Generator! Full Kitchen! Heat & A/C

Captain's Quarters 2BR Apartment. Walk to Everything!

8.8 out of 10, Excellent, (6)
The price is ¥25,272
¥38,340 total
includes taxes & fees
Aug 14 - Aug 15
Captain's Quarters 2BR Apartment. Walk to Everything!

Beautiful Studio in downtown Boothbay Harbor

9.0 out of 10, Wonderful, (8)
"Very cozy comfortable and convenient. Every thing we needed. "
Beautiful Studio in downtown Boothbay Harbor

Oceanfront, dog-friendly condo with Boothbay Harbor views & prime location

9.4 out of 10, Exceptional, (16)
"Loved the location, lots of activity but also very private and relaxing. Great place, everyone was really nice and friendly"
Oceanfront, dog-friendly condo with Boothbay Harbor views & prime location

Tranquil Seaside Cottage with Spectacular Views, Wifi & Washer/Dryer

2.0 star property
10.0 out of 10, Exceptional, (22)
"Beautiful location, comfortable beds and wonderful linens. This place was wonderful"
Tranquil Seaside Cottage with Spectacular Views, Wifi & Washer/Dryer

Cozy Waterfront Cottage with Dock

8.8 out of 10, Excellent, (3)
"Perfect Maine location! "
Cozy Waterfront Cottage with Dock

Enjoyable 1-bedroom rustic cottage in Southport.

10.0 out of 10, Exceptional, (10)
Enjoyable 1-bedroom rustic cottage in Southport.
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

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?

Boothbay Harbor Maine, Beautiful private Apartment : You might want to consider this vacation home rental near Chamberlain, which is located by the ocean and has a balcony, a garden, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, an oven, and a microwave.

How many vacation rentals will I find in Chamberlain?

With 3 Expedia vacation rentals, you're sure to find just the right place for your Chamberlain stay.

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.