Title: Pleasant Point Vacation Rentals from CA $449: Short-Term Rentals for 2026 | Expedia.ca

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## Check prices for these dates

In two weeks

[Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=553248635905812763&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=553248635905812763&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 8 - May 10](https://www.expedia.ca/Hotel-Search?regionId=553248635905812763&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 5 - Jun 7](https://www.expedia.ca/Hotel-Search?regionId=553248635905812763&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Pleasant Point vacation rentals

![Interior](https://images.trvl-media.com/lodging/90000000/89430000/89420800/89420791/w904h683x60y0-f337f923.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/90000000/89430000/89420800/89420791/262d6695.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/90000000/89430000/89420800/89420791/w907h683x60y0-47a4bb8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/90000000/89430000/89420800/89420791/w905h683x60y0-2642eebf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 2 Bedroom Close to Town Home

[](https://www.expedia.ca/Thomaston-Hotels-2-Bedroom-Close-To-Town-Home.h89420791.Hotel-Information)

Thomaston

9.0/10

Wonderful

(46 reviews)

"We loved our stay here! Check-in was easy and the host was responsive!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jessica H.

CA $141

CA $333 total

includes taxes & fees

Mar 1 - Mar 2

[](https://www.expedia.ca/Thomaston-Hotels-2-Bedroom-Close-To-Town-Home.h89420791.Hotel-Information)

![Lobby sitting area](https://images.trvl-media.com/lodging/96000000/95450000/95445100/95445009/2e12e11e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Panoramic Suite, 1 King Bed with Sofa bed, Balcony, Harbour View](https://images.trvl-media.com/lodging/96000000/95450000/95445100/95445009/f84c947d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Condo, Ocean View | Water view](https://images.trvl-media.com/lodging/96000000/95450000/95445100/95445009/b4a28964.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/96000000/95450000/95445100/95445009/8f885c43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Trade Winds on the Bay

[](https://www.expedia.ca/Rockland-Hotels-Trade-Winds-On-The-Bay.h95445009.Hotel-Information)

Rockland

8.6/10

Excellent

(341 reviews)

"Very nice place "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Robert

[](https://www.expedia.ca/Rockland-Hotels-Trade-Winds-On-The-Bay.h95445009.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/97000000/96700000/96696500/96696435/w903h683x60y0-77be3fd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/97000000/96700000/96696500/96696435/w906h683x59y0-3fc9c6c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/97000000/96700000/96696500/96696435/w506h683x259y0-707e34b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/97000000/96700000/96696500/96696435/w906h683x59y0-0b16edbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Peaceful, Centrally Located Home with Seasonal River Views

[](https://www.expedia.ca/Thomaston-Hotels-The-RiverView.h96696435.Hotel-Information)

Thomaston

9.4/10

Exceptional

(29 reviews)

"The house was clean and well stocked. It is is located in a cute little town."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Candace L.

CA $170

CA $373 total

includes taxes & fees

Feb 19 - Feb 20

[](https://www.expedia.ca/Thomaston-Hotels-The-RiverView.h96696435.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/119000000/118210000/118204400/118204396/938b4f7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/119000000/118210000/118204400/118204396/9ef0fd10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/119000000/118210000/118204400/118204396/f95889c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/119000000/118210000/118204400/118204396/47568e4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Boothbay-Hotels-Cozy-Renovated-Cabin-In-Central-Boothbay-Peaceful.h118204396.Hotel-Information)

Boothbay

7.8/10

Good

(7 reviews)

"This was perfect for our one night stay to visit the botanical gardens, it was only minutes away. Also very close to quite a few dinner and shopping options. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Nichole W.

CA $178

CA $269 total

includes taxes & fees

Feb 17 - Feb 18

[](https://www.expedia.ca/Boothbay-Hotels-Cozy-Renovated-Cabin-In-Central-Boothbay-Peaceful.h118204396.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/123000000/122590000/122586400/122586361/cfa18c66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/123000000/122590000/122586400/122586361/3c9c64ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/123000000/122590000/122586400/122586361/5a5195ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122590000/122586400/122586361/008602d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Romantic Coastal Escape near Harbor

[](https://www.expedia.ca/Rockport-Hotels-Romantic-Coastal-Escape-Near-Harbor.h122586361.Hotel-Information)

Rockport

CA $135

CA $292 total

includes taxes & fees

Feb 24 - Feb 25

[](https://www.expedia.ca/Rockport-Hotels-Romantic-Coastal-Escape-Near-Harbor.h122586361.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/91000000/90270000/90264700/90264685/29776283.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/91000000/90270000/90264700/90264685/9589a3f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90270000/90264700/90264685/93a0b9c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/91000000/90270000/90264700/90264685/a7299887.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Laughton House @ Pemaquid Beach

[](https://www.expedia.ca/New-Harbor-Hotels-Laughton-House-Pemaquid-Beach.h90264685.Hotel-Information)

Pemaquid Beach

10/10

Exceptional

(8 reviews)

"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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Dawn W.

CA $360

CA $874 total

includes taxes & fees

Feb 17 - Feb 18

[](https://www.expedia.ca/New-Harbor-Hotels-Laughton-House-Pemaquid-Beach.h90264685.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/45000000/44980000/44972100/44972039/4a7dcdde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/45000000/44980000/44972100/44972039/4cb410e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/45000000/44980000/44972100/44972039/93d8964d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/45000000/44980000/44972100/44972039/34f1eeb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Comfortable, Close to Town Home, with Oceanview.

[](https://www.expedia.ca/Owls-Head-Hotels-Comfortable.h44972039.Hotel-Information)

Owls Head

9.6/10

Exceptional

(86 reviews)

"Convenient location; host responsive; good towel supply. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Connie K.

CA $214

CA $449 total

includes taxes & fees

Feb 17 - Feb 18

[](https://www.expedia.ca/Owls-Head-Hotels-Comfortable.h44972039.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/122000000/121860000/121853200/121853117/6d9c5823.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/122000000/121860000/121853200/121853117/9ab13d04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121860000/121853200/121853117/f49a31d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121860000/121853200/121853117/61a45d93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Peaceful Intown Studio \~ Walk to Shops & Dining

[](https://www.expedia.ca/Newcastle-Hotels-Peaceful-Intown-Studio-Walk-To-Shops-Dining.h121853117.Hotel-Information)

Newcastle

7.0/10

Good

(2 reviews)

"The rental was exceptionally clean and neat. All appliances were like new. Parking was great. The bathroom could’ve used a plug in heater. We could easily hear people walking around on space above us. Nice views "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jason R.

CA $197

CA $245 total

includes taxes & fees

Feb 17 - Feb 18

[](https://www.expedia.ca/Newcastle-Hotels-Peaceful-Intown-Studio-Walk-To-Shops-Dining.h121853117.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78580000/78571300/78571271/dc6cc778.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, travel crib, free WiFi, bed sheets](https://images.trvl-media.com/lodging/79000000/78580000/78571300/78571271/3b72288d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78580000/78571300/78571271/e389e077.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/79000000/78580000/78571300/78571271/216fd53e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Shipbuilder’s Retreat sleeps 6, 5 minutes to Harbor

[](https://www.expedia.ca/East-Boothbay-Hotels-Shipbuilders-Retreat-Sleeps-6.h78571271.Hotel-Information)

East Boothbay

10/10

Exceptional

(46 reviews)

"Excellent, clean property. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Andy H.

CA $244

CA $637 total

includes taxes & fees

Feb 17 - Feb 18

[](https://www.expedia.ca/East-Boothbay-Hotels-Shipbuilders-Retreat-Sleeps-6.h78571271.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/123000000/122510000/122507900/122507840/d4674819.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/123000000/122510000/122507900/122507840/54a09d88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/123000000/122510000/122507900/122507840/81a123c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122510000/122507900/122507840/w3978h3000x0y0-d0dbda1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bright 2-Bedroom Apartment Near Downtown Thomaston

[](https://www.expedia.ca/Thomaston-Hotels-Terrific-2-Bedroom-House-In-Thomaston.h122507840.Hotel-Information)

Thomaston

10/10

Exceptional

(3 reviews)

"Very comfortable and convenient location. Super comfortable beds and living room furniture. Host was very quick to clean up the snow that fell overnight!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

tom w.

CA $163

CA $328 total

includes taxes & fees

Feb 17 - Feb 18

[](https://www.expedia.ca/Thomaston-Hotels-Terrific-2-Bedroom-House-In-Thomaston.h122507840.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92340000/92333500/92333487/w3000h1883x0y0-7746dac9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/93000000/92340000/92333500/92333487/b30dfaea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/93000000/92340000/92333500/92333487/ad79baef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, travel crib, free WiFi, bed sheets](https://images.trvl-media.com/lodging/93000000/92340000/92333500/92333487/f22ec6af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/East-Boothbay-Hotels-Shipbuilders-Retreat.h92333487.Hotel-Information)

East Boothbay

10/10

Exceptional

(22 reviews)

"Beautiful place, had everything we needed!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kathy H.

CA $337

CA $752 total

includes taxes & fees

Feb 17 - Feb 18

[](https://www.expedia.ca/East-Boothbay-Hotels-Shipbuilders-Retreat.h92333487.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/90000000/89660000/89655600/89655519/87772848.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, DVD player, books, music library](https://images.trvl-media.com/lodging/90000000/89660000/89655600/89655519/60fb6e31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89660000/89655600/89655519/6448c4d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/90000000/89660000/89655600/89655519/w651h433x0y5-e9133719.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hilltop 3BR Getaway w/ Chef BBQ, Fire Pit, Patios & Room to Relax

[](https://www.expedia.ca/Waldoboro-Hotels-Hilltop-3BR-Getaway-W-Chef-BBQ.h89655519.Hotel-Information)

Waldoboro

9.6/10

Exceptional

(9 reviews)

"Good visit overall."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Gerald S.

CA $362

CA $876 total

includes taxes & fees

Feb 17 - Feb 18

[](https://www.expedia.ca/Waldoboro-Hotels-Hilltop-3BR-Getaway-W-Chef-BBQ.h89655519.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/107000000/106810000/106809600/106809572/f2e89585.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106810000/106809600/106809572/861ec6f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/107000000/106810000/106809600/106809572/f2c203c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, in-room safe, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/107000000/106810000/106809600/106809572/e8096d2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Newly renovated motel garden rooms heart of boothbay affordable great hospitaliy

[](https://www.expedia.ca/Boothbay-Hotels-Newly-Renovated-Motel-Garden-Rooms-Heart-Of-Boothbay-Affordable-Great-Hospitaliy.h106809572.Hotel-Information)

Boothbay

6.0/10

(5 reviews)

"It had a very homey feel, was nice to stay at for the night and wasn’t far from town."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Audreyana P.

CA $453

CA $610 total

includes taxes & fees

Feb 17 - Feb 18

[](https://www.expedia.ca/Boothbay-Hotels-Newly-Renovated-Motel-Garden-Rooms-Heart-Of-Boothbay-Affordable-Great-Hospitaliy.h106809572.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/114000000/113340000/113334300/113334254/cbf78ef5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113340000/113334300/113334254/a2deacb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/114000000/113340000/113334300/113334254/129d3081.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/114000000/113340000/113334300/113334254/cef792fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Pemaquid Escape | Curated Comfort + Hot Tub

[](https://www.expedia.ca/Walpole-Hotels-New-Listing-Coastal-Charm-Comfort-In-Pemaquid.h113334254.Hotel-Information)

Walpole

10/10

Exceptional

(2 reviews)

"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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Melissa L.

CA $404

CA $928 total

includes taxes & fees

Feb 17 - Feb 18

[](https://www.expedia.ca/Walpole-Hotels-New-Listing-Coastal-Charm-Comfort-In-Pemaquid.h113334254.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117650000/117645800/117645730/2018e45a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/118000000/117650000/117645800/117645730/034798dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/118000000/117650000/117645800/117645730/9edd5bbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117650000/117645800/117645730/8d0738f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Newly Renovated Cozy Cove Cabin at White Anchor Inn

[](https://www.expedia.ca/Boothbay-Hotels-Newly-Renovated-Cozy-Cove-Cabin-At-White-Anchor-Inn.h117645730.Hotel-Information)

Boothbay

8.4/10

Very good

(6 reviews)

"As advertised, comfy bed cozy cabin. Would stay again "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Joseph B.

CA $453

CA $613 total

includes taxes & fees

Feb 23 - Feb 24

[](https://www.expedia.ca/Boothbay-Hotels-Newly-Renovated-Cozy-Cove-Cabin-At-White-Anchor-Inn.h117645730.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117680000/117677000/117676934/c585d217.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/118000000/117680000/117677000/117676934/cebcdd69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117680000/117677000/117676934/3e09eead.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/118000000/117680000/117677000/117676934/caec4ef8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Renovated The Driftwood Cabin at White Anchor Inn

[](https://www.expedia.ca/Boothbay-Hotels-Renovated-The-Driftwood-Cabin-At-White-Anchor-Inn.h117676934.Hotel-Information)

Boothbay

8.0/10

Very good

(2 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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Abra H.

CA $453

CA $622 total

includes taxes & fees

Feb 23 - Feb 24

[](https://www.expedia.ca/Boothbay-Hotels-Renovated-The-Driftwood-Cabin-At-White-Anchor-Inn.h117676934.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/116000000/115660000/115654600/115654518/023896ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/116000000/115660000/115654600/115654518/3da50d4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/116000000/115660000/115654600/115654518/042a9c3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/116000000/115660000/115654600/115654518/76a98a86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming Sheepscot Overlook Cottage

[](https://www.expedia.ca/Edgecomb-Hotels-Charming-Sheepscot-Overlook-Cottage.h115654518.Hotel-Information)

Edgecomb

10/10

Exceptional

(10 reviews)

"Great location, great view, great house, great time"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Carol P.

CA $885

CA $1,603 total

includes taxes & fees

Feb 28 - Mar 1

[](https://www.expedia.ca/Edgecomb-Hotels-Charming-Sheepscot-Overlook-Cottage.h115654518.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/97000000/96110000/96107000/96106993/ae0a6cfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/97000000/96110000/96107000/96106993/w648h433x0y2-fefe5d5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, DVD player, books, music library](https://images.trvl-media.com/lodging/97000000/96110000/96107000/96106993/d18cb0df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/97000000/96110000/96107000/96106993/af7f3a2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 7BR Hilltop Retreat · 2 Kitchens, Decks & Fire

[](https://www.expedia.ca/Waldoboro-Hotels-7BR-Hilltop-Retreat-2-Kitchens-Decks.h96106993.Hotel-Information)

Waldoboro

9.6/10

Exceptional

(5 reviews)

"The house and location was perfect, sitting around the fire pit to end the night was perfect "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

william h.

CA $877

CA $1,784 total

includes taxes & fees

Feb 17 - Feb 18

[](https://www.expedia.ca/Waldoboro-Hotels-7BR-Hilltop-Retreat-2-Kitchens-Decks.h96106993.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/100000000/99310000/99300500/99300493/dabb0fba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/100000000/99310000/99300500/99300493/2df8b15e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99310000/99300500/99300493/30d2c96e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/100000000/99310000/99300500/99300493/5c18e617.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 2-story apartment steps from the harbor & downtown

[](https://www.expedia.ca/Boothbay-Harbor-Hotels-2-Story-Apartment-Steps-From-The-Harbor-Downtown.h99300493.Hotel-Information)

Boothbay Harbor

6.0/10

(1 review)

"The apartment was quite cozy and clean. However, winter in Maine is unpredictable and must prepare for it. Huge liability risk not to have lighted parking area at night, walkways too narrow of snow and not well lit or shoveled."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Anonymous traveller

CA $409

CA $1,038 total

includes taxes & fees

Feb 17 - Feb 18

[](https://www.expedia.ca/Boothbay-Harbor-Hotels-2-Story-Apartment-Steps-From-The-Harbor-Downtown.h99300493.Hotel-Information)

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](https://expedia.ca/Hotel-Search?startDate=2026-03-02&endDate=2026-03-03&regionId=553248635905812763&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## Find vacation rentals that suit your style

Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=Pleasant+Point%2C+Maine%2C+United+States+of+America&regionId=553248635905812763&latLong=43.968261%2C-69.295739&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=APART_HOTEL)

Apartments

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Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Pleasant+Point%2C+Maine%2C+United+States+of+America&regionId=553248635905812763&latLong=43.968261%2C-69.295739&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=CABIN)

Condos

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Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Pleasant+Point%2C+Maine%2C+United+States+of+America&regionId=553248635905812763&latLong=43.968261%2C-69.295739&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=COTTAGE)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Pleasant+Point%2C+Maine%2C+United+States+of+America&regionId=553248635905812763&latLong=43.968261%2C-69.295739&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=VACATION_HOME)

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## Top Pleasant Point Hotel Reviews

![Hampton Inn & Suites Rockland](https://images.trvl-media.com/lodging/2000000/1470000/1460400/1460364/58471446_y.jpg)

### Hampton Inn & Suites Rockland

10/10 Excellent

"Clean rooms and staff were very friendly "

[](https://expedia.ca/Camden-Hotels-Hampton-Inn-Suites-Rockland.h1460364.Hotel-Information)

![The Country Inn at Camden Rockport](https://images.trvl-media.com/lodging/2000000/1570000/1570000/1569993/63281d3f_y.jpg)

### The Country Inn at Camden Rockport

10/10 Excellent

"Friendly staff, clean lodging"

[](https://expedia.ca/Camden-Hotels-The-Country-Inn-At-Camden-Rockport.h1569993.Hotel-Information)

![Harborline Hotel](https://images.trvl-media.com/lodging/12000000/11770000/11764500/11764432/427c5807_y.jpg)

### Harborline Hotel

10/10 Excellent

"Excellent stay!!"

[](https://expedia.ca/Rockland-Hotels-Harborline-Hotel.h11764432.Hotel-Information)

![Rockport Harbor Hotel](https://images.trvl-media.com/lodging/103000000/102950000/102944400/102944324/afe55a9f_y.jpg)

### Rockport Harbor Hotel

10/10 Excellent

"The room was beautiful and the atmosphere of the entire hotel was amazing ."

[](https://expedia.ca/Rockport-Hotels-Rockport-Harbor-Hotel.h102944324.Hotel-Information)

![Trade Winds on the Bay](https://images.trvl-media.com/lodging/96000000/95450000/95445100/95445009/6e8014d1_y.jpg)

### Trade Winds on the Bay

10/10 Excellent

"Clean, large room. Friendly staff. Great location@"

[](https://expedia.ca/Rockland-Hotels-Trade-Winds-On-The-Bay.h95445009.Hotel-Information)

![Flagship Inn and Suites](https://images.trvl-media.com/lodging/1000000/900000/894100/894021/8ffdcddf_y.jpg)

### Flagship Inn and Suites

10/10 Excellent

"Very convenient"

[](https://expedia.ca/Boothbay-Harbor-Hotels-Flagship-Inn-And-Suites.h894021.Hotel-Information)

![Rockland Harbor Hotel](https://images.trvl-media.com/lodging/14000000/13280000/13279200/13279193/0e52f770_y.jpg)

### Rockland Harbor Hotel

10/10 Excellent

"Great room, spacious and lovely view."

[](https://expedia.ca/Camden-Hotels-Rockland-Harbor-Hotel.h13279193.Hotel-Information)

![Cod Cove Inn, BW Signature Collection](https://images.trvl-media.com/lodging/35000000/34930000/34925200/34925132/d325545c_y.jpg)

### Cod Cove Inn, BW Signature Collection

10/10 Excellent

"The room was ample and inviting. "

[](https://expedia.ca/Boothbay-Harbor-Hotels-Cod-Cove-Inn.h34925132.Hotel-Information)

![Tugboat Inn](https://images.trvl-media.com/lodging/12000000/11900000/11898600/11898505/7562e385_y.jpg)

### Tugboat Inn

10/10 Excellent

"The room was comfortable, clean, and the staff were friendly. Thank you Tugboat Inn! "

[](https://expedia.ca/Boothbay-Harbor-Hotels-Tugboat-Inn.h11898505.Hotel-Information)

## Find out more about Pleasant Point

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 Pleasant Point. 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.   

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- [Vacation Homes in Pleasant Point ](https://expedia.ca/Pleasant-Point-Private-Vacation-Homes.d553248635905812763-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Cottages in Pleasant Point ](https://expedia.ca/Pleasant-Point-Cottages.d553248635905812763-aaCottages.Travel-Guide-Accommodation)
- [Apartments in Pleasant Point ](https://expedia.ca/Pleasant-Point-Apartments.d553248635905812763-aaApartments.Travel-Guide-Accommodation)
- [Cabin Rentals in Pleasant Point ](https://expedia.ca/Pleasant-Point-Cabins.d553248635905812763-aaCabins.Travel-Guide-Accommodation)
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- [B&B in Pleasant Point ](https://expedia.ca/Pleasant-Point-Bed-And-Breakfast.d553248635905812763-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Aparthotels in Pleasant Point ](https://expedia.ca/Pleasant-Point-Apart-Hotels.d553248635905812763-aaApartHotels.Travel-Guide-Accommodation)
- [Lodges in Pleasant Point ](https://expedia.ca/Pleasant-Point-Lodges.d553248635905812763-aaLodges.Travel-Guide-Accommodation)
- [Farmstay in Pleasant Point ](https://expedia.ca/Pleasant-Point-Agritourism.d553248635905812763-aaAgritourism.Travel-Guide-Accommodation)
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## Frequently asked questions

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