A harbor with several boats at sunset.

Port Clyde Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Port Clyde vacation rentals

A wooden deck with outdoor furniture, a table, and a view of the water.

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.
$223 nightly
The price is $243
Oct 30 - Oct 31
Total with taxes and fees
Gardenwalk Crest, Elevated Harbor Views, Deck and Village Setting
Lobby sitting area

2. Trade Winds on the Bay

Trade Winds on the Bay
3.5 star property
Rockland
8.6 out of 10, Excellent, (507 reviews)
"Its a place to stay."
United States
Todd
$82 nightly
The price is $89
Oct 20 - Oct 21
Total with taxes and fees
Trade Winds on the Bay
A compact bedroom with a bed, a small table, a bench, a TV, and a kitchenette.

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
$139 nightly
The price is $152
Oct 8 - Oct 9
Total with taxes and fees
Simplicity-Just what you need! STR24-20
A living room with a brown leather sofa, a wooden coffee table, and a window with curtains.

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.
$240 nightly
The price is $262
Nov 1 - Nov 2
Total with taxes and fees
2 Bedroom Close to Town Home
A wooden deck with Adirondack chairs and a grill.

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.
$230 nightly
The price is $251
Nov 2 - Nov 3
Total with taxes and fees
Bright 2-Bedroom Apartment Near Downtown Thomaston
A spacious living room with a black leather sofa, a glass coffee table, and large windows offering a view of greenery.

6. 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.
$273 nightly
The price is $298
Nov 2 - Nov 3
Total with taxes and fees
Peaceful, Centrally Located Home with Seasonal River Views
A wooden deck with a glass door leading to a room.

7. 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
$212 nightly
The price is $214
Oct 6 - Oct 7
Total with taxes and fees
Tiny Cottage Near Everything 10
Outdoor dining

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
$166 nightly
The price is $181
Oct 6 - Oct 7
Total with taxes and fees
Applecroft Cabin No. 3 - Modern off-grid cabin deep in the woods.
A bedroom with a large bed, a desk with two red chairs, a window with blinds, and a nightstand with a lamp.

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.
$216 nightly
The price is $227
Oct 26 - Oct 27
Total with taxes and fees
Cheerful Cottage Close to Everything 12
A bedroom with a bed, a bedside table, and a window with curtains.

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
$166 nightly
The price is $181
Oct 8 - Oct 9
Total with taxes and fees
Peaceful Intown Studio ~ Walk to Shops & Dining
A modern kitchen with a central island, built-in appliances, and a dining area with a high chair.

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.
$360 nightly
The price is $392
Oct 20 - Oct 21
Total with taxes and fees
Fire Pit & Grill, Movie Room, Workspace, A/C, Pets
A wooden cabin interior with a loft bedroom, a kitchen area, and a dining space.

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.
$224 nightly
The price is $236
Nov 3 - Nov 4
Total with taxes and fees
Cheerful Cottage with Loft 9
A room with a large window offering a view of a snowy landscape and a body of water.

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.
$340 nightly
The price is $371
Oct 25 - Oct 26
Total with taxes and fees
Comfortable, Close to Town Home, with Oceanview.
An aerial view of a marina with numerous boats docked and a small island with houses and greenery.

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.
$397 nightly
The price is $433
Nov 1 - Nov 2
Total with taxes and fees
Harbor/🦞 Pound Access & Views from Large Deck
A fenced garden area with a wooden gate, surrounded by greenery and trees.

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.
$189 nightly
The price is $206
Oct 6 - Oct 7
Total with taxes and fees
Newly renovated motel garden rooms heart of boothbay affordable great hospitaliy
A two-story house with a dark exterior, a balcony, and a well-maintained garden with rocks and plants.

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.
$546 nightly
The price is $595
Oct 13 - Oct 14
Total with taxes and fees
Oceanview Bungalow Style Home in Owls Head
A small cabin with a wooden deck, surrounded by trees in a wooded area.

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.
$263 nightly
The price is $278
Nov 3 - Nov 4
Total with taxes and fees
Spacious 1 Bedroom Cottage Close to Everything 3
A patio with a round glass table and two chairs, overlooking a grassy area with trees.

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.
$184 nightly
The price is $200
Oct 6 - Oct 7
Total with taxes and fees
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
A cozy living room with a wooden ceiling, a white sofa, a coffee table, and a dark armchair.

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.
$285 nightly
The price is $311
Oct 25 - Oct 26
Total with taxes and fees
A Spacious Vacation Cottage in Sheepscot Harbour
Two Adirondack chairs facing a body of water with a bridge in the background.

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.
$285 nightly
The price is $311
Oct 26 - Oct 27
Total with taxes and fees
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

Boothbay Harbor Inn

Boothbay Harbor Inn

10/10 Excellent
"This is our second time at Boothbay Harbor hotel. We love the cozy rooms on the water. Great location to the footbridge and Town. Great little Town with lots to do. We will be back."
Debra 1-night trip
Posted less than an hour ago
Boothbay Harbor Inn

Find out more about Port Clyde

Everything you need to know about Port Clyde vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Port Clyde vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Port Clyde vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Port Clyde vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Port Clyde. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Port Clyde in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $89 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Port Clyde rentals

At Expedia, we put the best Port Clyde vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Port Clyde rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Port Clyde vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Port Clyde. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.