A harbor with several boats at sunset.

Port Clyde Vacation Rentals

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Our top choices for Port Clyde vacation rentals

1. Gardenwalk Crest, Elevated Harbor Views, Deck and Village Setting

Gardenwalk Crest, Elevated Harbor Views, Deck and Village Setting
Port Clyde
9.8 out of 10, Exceptional, (59 reviews)
"Perfect!"
United States
Susan B.
The price is CA $278
CA $338 total
includes taxes & fees
Oct 30 - Oct 31
Gardenwalk Crest, Elevated Harbor Views, Deck and Village Setting

2. Trade Winds on the Bay

Trade Winds on the Bay
3.5 star property
Rockland
8.6 out of 10, Excellent, (502 reviews)
"Its a place to stay."
United States
Todd
The price is CA $117
CA $127 total
includes taxes & fees
Oct 30 - Oct 31
Trade Winds on the Bay

3. Simplicity-Just what you need! STR24-20

Simplicity-Just what you need! STR24-20
Rockland
9.8 out of 10, Exceptional, (35 reviews)
"Very nice tiny house in a quiet neighborhood. Easy walk to downtown"
United States
sarah
The price is CA $138
CA $216 total
includes taxes & fees
Oct 8 - Oct 9
Simplicity-Just what you need! STR24-20

4. 2 Bedroom Close to Town Home

2 Bedroom Close to Town Home
Thomaston
9.0 out of 10, Wonderful, (55 reviews)
"Perfect location to everything. Spacious house and clean. The directions for check in and check out where very clear and helpful!"
United States
Brianna M.
The price is CA $164
CA $366 total
includes taxes & fees
Nov 2 - Nov 3
2 Bedroom Close to Town Home

5. Bright 2-Bedroom Apartment Near Downtown Thomaston

Bright 2-Bedroom Apartment Near Downtown Thomaston
Thomaston
9.2 out of 10, Wonderful, (14 reviews)
"This place was nice and clean. The only thing was the service was spotty and WiFi was slow. Overall, great place and great location."
United States
Alexis H.
The price is CA $181
CA $352 total
includes taxes & fees
Nov 2 - Nov 3
Bright 2-Bedroom Apartment Near Downtown Thomaston

6. Peaceful, Centrally Located Home with Seasonal River Views

Peaceful, Centrally Located Home with Seasonal River Views
Thomaston
9.6 out of 10, Exceptional, (40 reviews)
"Great Stay!"
United States
Pastor Heidi G.
The price is CA $206
CA $419 total
includes taxes & fees
Nov 2 - Nov 3
Peaceful, Centrally Located Home with Seasonal River Views

7. Tiny Cottage Near Everything 10

Tiny Cottage Near Everything 10
Edgecomb
8.8 out of 10, Excellent, (5 reviews)
"Great location awesome place to take it easy for a few"
United States
Gene
The price is CA $129
CA $300 total
includes taxes & fees
Oct 5 - Oct 6
Tiny Cottage Near Everything 10

8. 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
The price is CA $211
CA $260 total
includes taxes & fees
Oct 5 - Oct 6
Applecroft Cabin No. 3 - Modern off-grid cabin deep in the woods.

9. Cheerful Cottage Close to Everything 12

Cheerful Cottage Close to Everything 12
Edgecomb
9.4 out of 10, Exceptional, (18 reviews)
"Cute place and very clean will definitely stay again "
United States
Tom C.
The price is CA $131
CA $313 total
includes taxes & fees
Oct 27 - Oct 28
Cheerful Cottage Close to Everything 12

10. Peaceful Intown Studio ~ Walk to Shops & Dining

Peaceful Intown Studio ~ Walk to Shops & Dining
Newcastle
9.0 out of 10, Wonderful, (11 reviews)
"Great location, excellent accommodations, perfect for our weekend adventure."
United States
Brian
The price is CA $206
CA $256 total
includes taxes & fees
Oct 8 - Oct 9
Peaceful Intown Studio ~ Walk to Shops & Dining

11. Fire Pit & Grill, Movie Room, Workspace, A/C, Pets

Fire Pit & Grill, Movie Room, Workspace, A/C, Pets
Thomaston
10.0 out of 10, Exceptional, (44 reviews)
"Wonderful place at a great price!"
United States
Stephen H.
The price is CA $263
CA $584 total
includes taxes & fees
Nov 2 - Nov 3
Fire Pit & Grill, Movie Room, Workspace, A/C, Pets

12. Cheerful Cottage with Loft 9

Cheerful Cottage with Loft 9
Edgecomb
10.0 out of 10, Exceptional, (5 reviews)
"Immaculate, very cute - “tiny cottage”We loved it!"
United States
Daniel B.
The price is CA $145
CA $332 total
includes taxes & fees
Oct 5 - Oct 6
Cheerful Cottage with Loft 9

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

Comfortable, Close to Town Home, with Oceanview.
Owls Head
9.6 out of 10, Exceptional, (101 reviews)
"Great location close to town"
United States
Rich W.
The price is CA $265
CA $516 total
includes taxes & fees
Nov 2 - Nov 3
Comfortable, Close to Town Home, with Oceanview.

14. Harbor/🦞 Pound Access & Views from Large Deck

Harbor/🦞 Pound Access & Views from Large Deck
Owls Head
9.6 out of 10, Exceptional, (82 reviews)
"Great place for a girls' weekend!! Had a wonderful stay!"
United States
Jeanette Q.
The price is CA $224
CA $611 total
includes taxes & fees
Nov 1 - Nov 2
Harbor/🦞 Pound Access & Views from Large Deck

15. 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 $192
CA $288 total
includes taxes & fees
Oct 3 - Oct 4
Newly renovated motel garden rooms heart of boothbay affordable great hospitaliy

16. Oceanview Bungalow Style Home in Owls Head

Oceanview Bungalow Style Home in Owls Head
Owls Head
9.8 out of 10, Exceptional, (82 reviews)
"We really enjoyed staying at this house! It was in a good location and was cute and cozy!"
United States
Victoria S.
The price is CA $288
CA $846 total
includes taxes & fees
Oct 13 - Oct 14
Oceanview Bungalow Style Home in Owls Head

17. Spacious 1 Bedroom Cottage Close to Everything 3

Spacious 1 Bedroom Cottage Close to Everything 3
Edgecomb
9.6 out of 10, Exceptional, (18 reviews)
"Great central location"
United States
Bruce O.
The price is CA $196
CA $394 total
includes taxes & fees
Nov 2 - Nov 3
Spacious 1 Bedroom Cottage Close to Everything 3

18. 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, (15 reviews)
"Great stay! Pet friendly, super responsive host and excellent location!"
United States
Cassie M.
The price is CA $186
CA $281 total
includes taxes & fees
Oct 5 - Oct 6
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything

19. A Spacious Vacation Cottage in Sheepscot Harbour

A Spacious Vacation Cottage in Sheepscot Harbour
Edgecomb
10.0 out of 10, Exceptional, (70 reviews)
"Great place and great restaurants."
United States
Julie D.
The price is CA $212
CA $434 total
includes taxes & fees
Oct 26 - Oct 27
A Spacious Vacation Cottage in Sheepscot Harbour

20. 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, (89 reviews)
"Lovely cottage with a great view."
United States
Ann M.
The price is CA $212
CA $434 total
includes taxes & fees
Oct 26 - Oct 27
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 Port Clyde Hotel Reviews

Find out more about Port Clyde

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 Port Clyde. 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 vacation rentals in Port Clyde?

Yes, there are vacation rentals near popular attractions in Port Clyde, or you can choose a more secluded option if you want a relaxing place to stay.

What's the top vacation rental that Port Clyde has to offer?

Oceanview Bungalow Style Home in Owls Head: This vacation home rental outside of Port Clyde is located by the ocean and has a balcony, a terrace, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals will I find in Port Clyde?

With 17 Expedia vacation rentals, you're sure to find just the right place for your Port Clyde stay.

What’s there to see and do in Port Clyde?

Explore the area and family-friendly sights such as Maine State Prison Store, or get out into nature at a spot like St. George River. Marshall Point Lighthouse and Owls Head Transportation Museum are a couple of places you'll find in the larger area.

What are vacation rentals like in Port Clyde?

Vacation rentals are privately owned properties you can stay in for a long or short time in Port Clyde. Vacation rentals offer amenities such as hot tubs, fire pits, and patios to help you enjoy your stay. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive option for family trips.