A harbor with several boats at sunset.

Port Clyde Vacation Rentals

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Our top choices for Port Clyde vacation rentals

1. Trade Winds on the Bay

Trade Winds on the Bay
3.5 star property
Rockland
8.6 out of 10, Excellent, (521 reviews)
"Everything was clean, easy check in process and convenient location, walking distance to multiple restaurants."
United States
Bill
The price is CA $153
CA $167 total
includes taxes & fees
Nov 23 - Nov 24
Trade Winds on the Bay

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

Comfortable, Close to Town Home, with Oceanview.
Owls Head
9.6 out of 10, Exceptional, (102 reviews)
"We weren’t even there for 24 hours. It was a great stop on the coast. Close to Rockland and a nice view of the ocean."
United States
Ted H.
The price is CA $241
CA $487 total
includes taxes & fees
Nov 23 - Nov 24
Comfortable, Close to Town Home, with Oceanview.

3. Peaceful, Centrally Located Home with Seasonal River Views

Peaceful, Centrally Located Home with Seasonal River Views
Thomaston
9.6 out of 10, Exceptional, (41 reviews)
"Great Stay!"
United States
Pastor Heidi G.
The price is CA $182
CA $392 total
includes taxes & fees
Nov 9 - Nov 10
Peaceful, Centrally Located Home with Seasonal River Views

4. Peaceful Intown Studio ~ Walk to Shops & Dining

Peaceful Intown Studio ~ Walk to Shops & Dining
Newcastle
9.0 out of 10, Wonderful, (12 reviews)
"Great location, excellent accommodations, perfect for our weekend adventure."
United States
Brian
The price is CA $203
CA $252 total
includes taxes & fees
Oct 29 - Oct 30
Peaceful Intown Studio ~ Walk to Shops & Dining

5. 2 Bedroom Close to Town Home

2 Bedroom Close to Town Home
Thomaston
8.8 out of 10, Excellent, (58 reviews)
"It was in a perfect location for our planned trip. Thank you"
United States
Nita S.
The price is CA $161
CA $363 total
includes taxes & fees
Nov 2 - Nov 3
2 Bedroom Close to Town Home

6. Bright 2-Bedroom Apartment Near Downtown Thomaston

Bright 2-Bedroom Apartment Near Downtown Thomaston
Thomaston
9.2 out of 10, Wonderful, (16 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 $168
CA $339 total
includes taxes & fees
Oct 26 - Oct 27
Bright 2-Bedroom Apartment Near Downtown Thomaston

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

Harbor/🦞 Pound Access & Views from Large Deck
Owls Head
9.6 out of 10, Exceptional, (84 reviews)
"Great place for a girls' weekend!! Had a wonderful stay!"
United States
Jeanette Q.
The price is CA $199
CA $579 total
includes taxes & fees
Nov 1 - Nov 2
Harbor/🦞 Pound Access & Views from Large Deck

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

Simplicity-Just what you need! STR24-20
Rockland
9.8 out of 10, Exceptional, (37 reviews)
"This was such a super cute place. Great little get away. Very clean! I would definitely recommend this place if you are in the area!"
United States
Beth
The price is CA $136
CA $213 total
includes taxes & fees
Oct 27 - Oct 28
Simplicity-Just what you need! STR24-20

9. In-town, coastal + relaxing in Rockland

In-town, coastal + relaxing in Rockland
Rockland
10.0 out of 10, Exceptional, (57 reviews)
"Great location, great house! It was a perfect getaway for us, highly recommend."
United States
Rob J.
The price is CA $348
CA $784 total
includes taxes & fees
Oct 28 - Oct 29
In-town, coastal + relaxing in Rockland

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, (63 reviews)
"Tucked away in a wooded lot, quick drive to Boothbay Harbor. Side by side units are great for friends or families traveling together."
United States
Carly C.
The price is CA $339
CA $771 total
includes taxes & fees
Oct 24 - Oct 25
Shipbuilder’s Retreat sleeps 6, 5 minutes to Harbor

11. “Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
Nobleboro
10.0 out of 10, Exceptional, (51 reviews)
"We loved everything about this place! It’s beautifully decorated and feels like a home away from away. The host was wonderful and made it easy to communicate with her. The view from the deck is so pretty! I loved having a cup of tea out there and looking at the water. It was a perfect spot! We are so grateful!"
United States
Rhiannon A.
The price is CA $259
CA $498 total
includes taxes & fees
Oct 26 - Oct 27
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

12. Tiny Cottage Near Everything 10

Tiny Cottage Near Everything 10
Edgecomb
9.0 out of 10, Wonderful, (6 reviews)
"Great location awesome place to take it easy for a few"
United States
Gene
The price is CA $124
CA $292 total
includes taxes & fees
Oct 26 - Oct 27
Tiny Cottage Near Everything 10

13. 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 $203
CA $253 total
includes taxes & fees
Oct 24 - Oct 25
Applecroft Cabin No. 3 - Modern off-grid cabin deep in the woods.

14. Across the road from Pemaquid Beach: A 4-bedroom 19th-century Maine home

Across the road from Pemaquid Beach: A 4-bedroom 19th-century Maine home
Pemaquid Beach
10.0 out of 10, Exceptional, (11 reviews)
"Comfortable, clean and beautiful "
United States
Corina
The price is CA $427
CA $957 total
includes taxes & fees
Nov 15 - Nov 16
Across the road from Pemaquid Beach: A 4-bedroom 19th-century Maine home

15. Come Spring Farm Airstream , Lake & farm animals

Come Spring Farm Airstream , Lake & farm animals
Union
8.4 out of 10, Very good, (5 reviews)
"Pet Friendly, Great surroundings, close to popular tourist towns in Maine"
United States
Thomas W.
The price is CA $231
CA $359 total
includes taxes & fees
Oct 24 - Oct 25
Come Spring Farm Airstream , Lake & farm animals

16. Peaceful Lake waterfront! Full Kitchen! Ht&AC! Is Private entry waterside in-law

Peaceful Lake waterfront! Full Kitchen! Ht&AC! Is Private entry waterside in-law
Boothbay Harbor
10.0 out of 10, Exceptional, (128 reviews)
"This place was the definition of relaxation! The access to West Harbor "Pond" (it's huge -- more like a lake!) was unbeatable! We were able to use the provided kayaks to explore the little islands in the water and to come really close to a pair of loons!"
United States
Melinda M.
The price is CA $280
CA $481 total
includes taxes & fees
Nov 10 - Nov 11
Peaceful Lake waterfront! Full Kitchen! Ht&AC! Is Private entry waterside in-law

17. 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, (90 reviews)
"Lovely cottage with a great view."
United States
Ann M.
The price is CA $188
CA $409 total
includes taxes & fees
Oct 29 - Oct 30
Spectacular Waterfront Cottage: Charming Getaway on The Sheepscot River

18. 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 $134
CA $316 total
includes taxes & fees
Oct 27 - Oct 28
Cheerful Cottage with Loft 9

19. Dome 3 at Come Spring Farm Glamping - Alpaca Farm

Dome 3 at Come Spring Farm Glamping - Alpaca Farm
Union
8.8 out of 10, Excellent, (16 reviews)
"Beautiful location and a unique stay."
United States
Sabrina D.
The price is CA $231
CA $337 total
includes taxes & fees
Nov 1 - Nov 2
Dome 3 at Come Spring Farm Glamping - Alpaca Farm

20. A Spacious Vacation Cottage in Sheepscot Harbour

A Spacious Vacation Cottage in Sheepscot Harbour
Edgecomb
10.0 out of 10, Exceptional, (71 reviews)
"Great place and great restaurants."
United States
Julie D.
The price is CA $188
CA $411 total
includes taxes & fees
Oct 26 - Oct 27
A Spacious Vacation Cottage in Sheepscot Harbour
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.