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Holiday Rentals in Drakes Island

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Drakes Island holiday rentals

A circular stone fire pit surrounded by Adirondack chairs in a grassy outdoor area with a tree overhead and a white fence in the background.

1. Elmwood Resort Hotel

Elmwood Resort Hotel
3.0 star property
Wells
9.4 out of 10, Exceptional, (477 reviews)
"I like that we can all stay together but have our own space"
United States
Joan
The price is €160
includes taxes & fees
15 Nov - 16 Nov
Elmwood Resort Hotel
A row of beige multi-story buildings with brown roofs, arranged in a linear fashion with a parking lot in the foreground.

2. Village by the Sea

Village by the Sea
3.5 star property
Wells
9.0 out of 10, Wonderful, (568 reviews)
"The rental is very spacious and the price is reasonable. It’s clean and beautiful."
United States
Quirica
The price is €202
includes taxes & fees
23 Nov - 24 Nov
Village by the Sea
A beach with rocks and waves.

3. Wellington Manor #140 first-floor corner studio with patio and sauna

Wellington Manor #140 first-floor corner studio with patio and sauna
Wells
9.4 out of 10, Exceptional, (9 reviews)
"The place was small but highly effective to stay. Great little kitchen full of utensils, table to eat, light and air via windows, the bed was comfortable and so were the chairs. The bathroom had two sinks and a roomy shower. Parking was ample and location close to things. And if you have friends in the area, great place to invite over for a meal or to hang in the clubhouse for a game of billiards or a swim. Would definitely stay here again. The one downside was a musty smell, but that tends to...
United States
Scott F.
The price is €319
includes taxes & fees
12 Nov - 13 Nov
Wellington Manor #140 first-floor corner studio with patio and sauna
A beach path leading to the ocean with a wooden fence on one side and dense foliage on the other.

4. Coastal Condo with Pool at Wells Beach

Coastal Condo with Pool at Wells Beach
Wells Beach
10.0 out of 10, Exceptional, (6 reviews)
"Great space, clean and easy check in and out. Highly recommend!"
United States
Rachael B.
Coastal Condo with Pool at Wells Beach
A marina with multiple boats docked, a wooden pier, and houses in the background.

5. NEW Beachside Wells Beach Condo with Pool

NEW Beachside Wells Beach Condo with Pool
Wells Beach
10.0 out of 10, Exceptional, (2 reviews)
"The only entrance to the unit is unusual which is via the outdoor pool area. Stay was great!"
United States
joan p.
The price is €331
includes taxes & fees
12 Nov - 13 Nov
NEW Beachside Wells Beach Condo with Pool
A spacious living area with a high ceiling, a dining table with chairs, a sofa, a coffee table, and a TV.

6. Generic Two Bedroom- Stair access only

Generic Two Bedroom- Stair access only
Wells
9.0 out of 10, Wonderful, (6 reviews)
"Our 2 bedroom unit was beautiful - very clean well appointed. Four adults stayed here very comfortably. Really liked having washer and dryer. Check in was easy. Didn’t have to do a bunch of “housekeeping” before checking out - just take out the trash and run the dishwasher!"
United States
Julie R.
The price is €222
includes taxes & fees
24 Nov - 25 Nov
Generic Two Bedroom- Stair access only
A cozy living room with a large window, a beige sofa, and a small table with glasses and a candle.

7. Salt Box by the Sea: Water View - Charming 3-bedroom Cottage in Wells!

Salt Box by the Sea: Water View - Charming 3-bedroom Cottage in Wells!
Wells
9.6 out of 10, Exceptional, (40 reviews)
"This cottage was the perfect size for 5 adults in the family and convenient location for exploring"
United States
Andrea
The price is €412
includes taxes & fees
16 Nov - 17 Nov
Salt Box by the Sea: Water View - Charming 3-bedroom Cottage in Wells!
A bedroom with a view of the ocean through large windows, a bed with a white blanket, a breakfast tray with eggs and orange juice, and a bedside table with a glass.

8. Ocean Views• Beach Access• Central Location• A/C

Ocean Views• Beach Access• Central Location• A/C
Wells Beach
10.0 out of 10, Exceptional, (7 reviews)
"The house was clean and comfortable. The views are awesome. The beach is a short walk away and there is a lobster/ice cream shop between the house and beach. Excellent location. Communication with the host was flawless. The nature reserve out back was an added bonus and we enjoyed our nightly visits by the deer. There were multiple families of ducks right across the street as well."
United States
Karen B.
Ocean Views• Beach Access• Central Location• A/C
A dining area with a wooden table, chairs, and a potted plant with blue flowers.

9. Welcome to the Sunshine Shack, a Unique Bright Cottage with Bold Ocean Views!

Welcome to the Sunshine Shack, a Unique Bright Cottage with Bold Ocean Views!
Moody Point
9.8 out of 10, Exceptional, (79 reviews)
"The cottage was beautifully decorated and very clean. It was accurately pictured. We loved sitting on the deck with the ocean views and breeze! The kitchen was well equipped and easy to navigate. Close to beaches and restaurants. Thanks!!"
United States
Kim O.
The price is €593
includes taxes & fees
25 Nov - 26 Nov
Welcome to the Sunshine Shack, a Unique Bright Cottage with Bold Ocean Views!
A dining area with a wooden table, wicker chairs, and a hanging light fixture.

10. Twenty Shore - 2 Ocean Suite

Twenty Shore - 2 Ocean Suite
Ogunquit
9.2 out of 10, Wonderful, (26 reviews)
"A wonderful property in the heart of Olgonquit! Perfect place for a mother daughter weekend trip! Property is clean, well furnished, and in the best location. The hostess is super responsive--I had questions about parking that were answered immediately. Highly recommend!"
United States
Mary P.
The price is €311
includes taxes & fees
24 Nov - 25 Nov
Twenty Shore - 2 Ocean Suite
A modern living room with a flat-screen TV, a round coffee table, and a sofa.

11. Twenty Shore - 4 Beach Suite

Twenty Shore - 4 Beach Suite
Ogunquit
9.4 out of 10, Exceptional, (30 reviews)
"Fantastic stay close to shops, restaurants and the beach. We will be back."
United States
James A.
The price is €315
includes taxes & fees
12 Nov - 13 Nov
Twenty Shore - 4 Beach Suite
A compact living space with a grey brick wall, a grey sofa, a white wicker chair, and a small table. A kitchen is visible through an open doorway.

12. Kennebunk - Kennebunkport Beach House with Heated Swimming Pool!

Kennebunk - Kennebunkport Beach House with Heated Swimming Pool!
Kennebunk
9.4 out of 10, Exceptional, (69 reviews)
"Great stay."
United States
Ryan R.
The price is €752
includes taxes & fees
12 Nov - 13 Nov
Kennebunk - Kennebunkport Beach House with Heated Swimming Pool!
A beach with people, umbrellas, and houses in the background.

13. A Wave From It All with Hot tub

A Wave From It All with Hot tub
Kennebunk
The price is €946
includes taxes & fees
12 Nov - 13 Nov
A Wave From It All with Hot tub
A modern kitchen with white cabinetry, a wooden ceiling, and a central island with stools.

14. Charming Kennebunk Cape - Walk to Dock Square!

Charming Kennebunk Cape - Walk to Dock Square!
Kennebunk
9.8 out of 10, Exceptional, (43 reviews)
"Perfect location and the home was larger than expected! Plenty of space for several families, comfortable beds, extra (comfy) cots and everything you need for a great stay!"
United States
Hilary C.
The price is €715
includes taxes & fees
12 Nov - 13 Nov
Charming Kennebunk Cape - Walk to Dock Square!
A modern kitchen with a marble countertop, a coffee maker, and pendant lighting.

15. Cute and Cozy Cape in the Heart of Ogunquit Center

Cute and Cozy Cape in the Heart of Ogunquit Center
Ogunquit
10.0 out of 10, Exceptional, (43 reviews)
"We loved our time in ogunquit. The house is very charming and it has everything you need. Even things we didn’t know we needed! Location could not be better. We will for sure be back next summer!"
Canada
Maria
The price is €413
includes taxes & fees
15 Nov - 16 Nov
Cute and Cozy Cape in the Heart of Ogunquit Center
A modern living room with a sofa, a round coffee table, and a kitchen area in the background.

16. Walk to Dock Square, 1.2 Mi to Gooch's Beach, Hot Tub -- Pine Tree Place

Walk to Dock Square, 1.2 Mi to Gooch's Beach, Hot Tub -- Pine Tree Place
Kennebunk
10.0 out of 10, Exceptional, (9 reviews)
"Very nice property - extremely neat, clean and comfortable. "
United States
Amy
The price is €550
includes taxes & fees
16 Nov - 17 Nov
Walk to Dock Square, 1.2 Mi to Gooch's Beach, Hot Tub -- Pine Tree Place
A modern kitchen with wooden cabinets, a central island with bar stools, and a dining area with chairs.

17. Cozy home 1mi. to beaches/shops/dining, Hot tub, big PATIO, Pvt yard, fire pit

Cozy home 1mi. to beaches/shops/dining, Hot tub, big PATIO, Pvt yard, fire pit
Kennebunk
9.8 out of 10, Exceptional, (30 reviews)
"Great location. Near the beach. Excellent set up for family with kids."
United States
Jaime G.
The price is €830
includes taxes & fees
12 Nov - 13 Nov
Cozy home 1mi. to beaches/shops/dining, Hot tub, big PATIO, Pvt yard, fire pit
A waterfront property with a large house featuring multiple windows and a balcony, a dock with a sailboat, and a calm body of water reflecting the buildings.

18. Historic Kennebunkport home only 0.3 miles to Dock Square

Historic Kennebunkport home only 0.3 miles to Dock Square
Kennebunkport
10.0 out of 10, Exceptional, (96 reviews)
"Fantastic location and a wonderful place to spend time while in Kennebunkport. We’ll definitely be back!"
United States
Chris P.
The price is €453
includes taxes & fees
12 Nov - 13 Nov
Historic Kennebunkport home only 0.3 miles to Dock Square
A dining area with a wooden table, wicker chairs, and a hanging light fixture.

19. Twenty Shore - 3 Sun Suite

Twenty Shore - 3 Sun Suite
Ogunquit
9.0 out of 10, Wonderful, (4 reviews)
"Great location!"
United States
Vanessa
The price is €326
includes taxes & fees
12 Nov - 13 Nov
Twenty Shore - 3 Sun Suite
A bathroom with a black countertop, a wicker basket, a wooden bowl, and a rack with towels and a robe.

20. Shamrock by the Sea Hot Tub Arcade Basketball Court & Beach Fun

Shamrock by the Sea Hot Tub Arcade Basketball Court & Beach Fun
Moody
10.0 out of 10, Exceptional, (18 reviews)
"The property is beautifully decorated, clean, well supplied & in excellent condition. The kids thoroughly enjoyed the game room & we all loved sitting around the fire pit & several used the hot tub. We definitely recommend Walking the Marginal Way, (the scenery is spectacular) & shopping in Ogunquit & Kennebunkport. It was an excellent choice for a family reunion!"
United States
Patricia A.
Shamrock by the Sea Hot Tub Arcade Basketball Court & Beach Fun
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 Drakes Island Hotel Reviews

The Meadowmere Resort

The Meadowmere Resort

10/10 Excellent
"We have stayed at the Meadowmere Resort a few times. We really love the location of this resort. It's super convenient to the main thoroughfare, too!"
Susan 2-night trip
Posted 13 hours ago
The Meadowmere Resort

Find out more about Drakes Island

Everything you need to know about Drakes Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Drakes Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 Drakes Island holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Drakes Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Drakes Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Drakes Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Drakes Island holiday rentals we have selected for you start as low as €160 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Drakes Island rentals

At Expedia, we put the best Drakes Island holiday 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 Drakes Island 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 Drakes Island holiday.

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