Great Diamond Island Vacation Rentals

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Check prices for these dates

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

Our top choices for Great Diamond Island vacation rentals

A modern kitchen with a central island, bar stools, a dining table, and a built-in oven.

1. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (131 reviews)
"It was so spacious, kitchen area was well kept and they have QR codes to help travels understand how to use certain things"
United States
Branden
$264 nightly
The price is $281
Nov 30 - Dec 1
Total with taxes and fees
The Weldon Hotel
A multi-story building with a stone facade, large windows, and a corner entrance.

2. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (19 reviews)
"Truly a wonderful place with an unbeatable location. Highly recommend for a visit to Portland."
United States
Eric
$361 nightly
The price is $393
Dec 7 - Dec 8
Total with taxes and fees
Evalina Hotel
A beach with clear water, people swimming, and houses in the background.

3. Willard By the Sea - 30 ft to the beach- 2nd floor

Willard By the Sea - 30 ft to the beach- 2nd floor
Willard
10.0 out of 10, Exceptional, (16 reviews)
"Fantastic beach location and comfortable unit equipped with air conditioning (essential during the heat wave that occurred during our stay). Clean rooms, good size and full kitchen; comfortable furnishings.Only caution is that this is a beach-side location and appears to have a bit of a price premium for that reason. It’s justified but only if you’re planning to make good use of the beach."
United States
Gerald B.
$443 nightly
The price is $463
Nov 17 - Nov 18
Total with taxes and fees
Willard By the Sea - 30 ft to the beach- 2nd floor
A room with a white table, two chairs, a plant on a stool, and a white wall with a blue trim.

4. 2-bedroom apartment in Portland, ME with WiFi, AC. Enjoy your stay!

2-bedroom apartment in Portland, ME with WiFi, AC. Enjoy your stay!
Munjoy Hill
8.8 out of 10, Excellent, (3 reviews)
"Was right in the area we wanted and in a nice neighborhood. Would def stay again!"
United States
Amalia C.
$300 nightly
The price is $327
Nov 10 - Nov 11
Total with taxes and fees
2-bedroom apartment in Portland, ME with WiFi, AC. Enjoy your stay!
A beach with a wooden chair and a small building in the background.

5. Arlie`s Digs! - One Block To Willard Beach!

Arlie`s Digs! - One Block To Willard Beach!
Willard Beach
10.0 out of 10, Exceptional, (73 reviews)
"Great stay!"
United States
Jason M.
$375 nightly
The price is $409
Nov 30 - Dec 1
Total with taxes and fees
Arlie`s Digs! - One Block To Willard Beach!
A house with a wooden front door, a stone staircase, and a porch with a wooden railing.

6. Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
East Deering
10.0 out of 10, Exceptional, (85 reviews)
"Absolutely perfect rental!Great location with an amazing view!"
United States
Mike G.
$947 nightly
The price is $1,032
Nov 12 - Nov 13
Total with taxes and fees
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
A gray house with a black front door, white trim, and a number 70 sign.

7. Vintage Maine & Modern Convenience in Portlands Exclusive East End

Vintage Maine & Modern Convenience in Portlands Exclusive East End
Munjoy Hill
9.8 out of 10, Exceptional, (64 reviews)
"The apartment is very comfortable with everything we needed We loved the quiet neighborhood and the location was really great within walking distance to both the beach area and downtown shops & restaurants."
United States
maureen
$419 nightly
The price is $457
Nov 22 - Nov 23
Total with taxes and fees
Vintage Maine & Modern Convenience in Portlands Exclusive East End
A modern living room with a sofa, coffee table, and chairs, a kitchen with wooden cabinets, and large windows offering a view.

8. Harborview - Curated East End Escape w/ Parking

Harborview - Curated East End Escape w/ Parking
Munjoy Hill
10.0 out of 10, Exceptional, (14 reviews)
"5 star in every way"
United States
Doug F.
$630 nightly
The price is $705
Nov 10 - Nov 11
Total with taxes and fees
Harborview - Curated East End Escape w/ Parking
A storefront with the sign 'OYSTERS' and a 'RAW BAR' sign above the entrance. There are outdoor seating areas with tables and chairs.

9. Modern & Sunny East End House.

Modern & Sunny East End House.
Munjoy Hill
10.0 out of 10, Exceptional, (51 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
$459 nightly
The price is $511
Nov 10 - Nov 11
Total with taxes and fees
Modern & Sunny East End House.
A building named Willard Square with a storefront and a red vehicle parked outside.

10. Willard Square Family Home

Willard Square Family Home
Willard Beach
9.8 out of 10, Exceptional, (13 reviews)
"Thoroughly enjoyed this house! "
United States
David W.
$589 nightly
The price is $624
Nov 12 - Nov 13
Total with taxes and fees
Willard Square Family Home
A modern kitchen with a central island, stainless steel appliances, and contemporary artwork.

11. A Peaceful Oasis on Munjoy Hill: 1st flr - 3BR + parking

A Peaceful Oasis on Munjoy Hill: 1st flr - 3BR + parking
Munjoy Hill
10.0 out of 10, Exceptional, (11 reviews)
"Great spot. Roomy. Close to shops and ferries. It had everything we needed to see Portland."
United States
Benton M.
$328 nightly
The price is $357
Nov 10 - Nov 11
Total with taxes and fees
A Peaceful Oasis on Munjoy Hill: 1st flr - 3BR + parking
A room with two wicker chairs, a potted plant, and a view of a body of water and buildings through large windows with blinds.

12. 2-Bedroom Apartment Steps from Eastern Prom - Walk to Everything!

2-Bedroom Apartment Steps from Eastern Prom - Walk to Everything!
Munjoy Hill
10.0 out of 10, Exceptional, (6 reviews)
"Lovely clean property in a really great location. Walkable to town center! Perfect !"
United States
Anonymous traveler
$365 nightly
The price is $397
Nov 10 - Nov 11
Total with taxes and fees
2-Bedroom Apartment Steps from Eastern Prom - Walk to Everything!
A garden with a stone bridge over a small stream, surrounded by various plants and flowers.

13. Peaceful Oasis on Munjoy Hill 2nd flr 3BR parking

Peaceful Oasis on Munjoy Hill 2nd flr 3BR parking
Munjoy Hill
9.8 out of 10, Exceptional, (7 reviews)
"Just perfect. Clean, very nicely furnished and decorated, well equipped apartment was everything we needed in an absolutely fantastic location. Owner was friendly and helpful and we loved our stay."
United States
juliet a.
$347 nightly
The price is $379
Nov 16 - Nov 17
Total with taxes and fees
Peaceful Oasis on Munjoy Hill 2nd flr 3BR parking
A brick wall with a logo and the text 'THE SEND BREWING CO.'

14. Peaceful & minutes from Old Port w/private parking

Peaceful & minutes from Old Port w/private parking
Knightville
9.8 out of 10, Exceptional, (13 reviews)
"Cute, convenient spot!"
United States
Kelly S.
$217 nightly
The price is $237
Nov 10 - Nov 11
Total with taxes and fees
Peaceful & minutes from Old Port w/private parking
A brick wall with a logo and the text 'THE SEND BREWING CO.'

15. Sunny Spot with Private Parking

Sunny Spot with Private Parking
Knightville
9.8 out of 10, Exceptional, (38 reviews)
"Great property. Cute place. Note that there are very steep steps to get into the place, which is a conveyed attic."
United States
Greg Z.
$183 nightly
The price is $200
Nov 10 - Nov 11
Total with taxes and fees
Sunny Spot with Private Parking
A modern kitchen with a central island, two stools, skylights, and a view of the outdoors.

16. East End Guesthouse

East End Guesthouse
Munjoy Hill
10.0 out of 10, Exceptional, (7 reviews)
"Fabulous stay!! Felt like we were living in a Crate & Barrel catalog. Great location. "
United States
Ashleigh F.
$339 nightly
The price is $370
Nov 17 - Nov 18
Total with taxes and fees
East End Guesthouse
A kitchen with a wooden island, black bar stools, a hanging light fixture, and a framed botanical print on the wall.

17. Spacious 4-bedroom house located in the heart of Portland, ME.

Spacious 4-bedroom house located in the heart of Portland, ME.
Munjoy Hill
10.0 out of 10, Exceptional, (23 reviews)
"Great space for our needs: three generations for a graduation weekend!"
United States
Matt H.
$771 nightly
The price is $840
Nov 10 - Nov 11
Total with taxes and fees
Spacious 4-bedroom house located in the heart of Portland, ME.
A bathroom with white tiles, a shower, and a mirror.

18. East end. Walk to food, beer and downtown fun.

East end. Walk to food, beer and downtown fun.
Munjoy Hill
9.8 out of 10, Exceptional, (47 reviews)
"A great place to stay while exploring and visiting Portland! Great communication, easy process, and would definitely stay again if we visit Franklin"
United States
Jordan M.
$320 nightly
The price is $341
Nov 12 - Nov 13
Total with taxes and fees
East end. Walk to food, beer and downtown fun.
A modern living room with a brown leather sofa, a wooden sliding door, and a framed artwork on the wall.

19. Hip & Luxurious Garden Retreat for Families, Foodies & Adventurers

Hip & Luxurious Garden Retreat for Families, Foodies & Adventurers
Munjoy Hill
10.0 out of 10, Exceptional, (60 reviews)
"Everything from booking to checkout was outstanding! Very clean, great location, easy parking and walking to town. The host quickly communicates; highly recommend this place for your stay in Portland!"
United States
Kirsten Z.
$737 nightly
The price is $804
Nov 10 - Nov 11
Total with taxes and fees
Hip & Luxurious Garden Retreat for Families, Foodies & Adventurers
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 Great Diamond Island Hotel Reviews

A two-story hotel with a balcony on the second floor, a sign reading "The Inn on Peaks Island," and a flag in front.
Inn On Peaks Island

Inn On Peaks Island

Inn On Peaks Island
Peaks Island

10/10 Excellent

Beautiful spot right next to the ferry drop off. Views of the ocean, outdoor dining, and lovely rooms.
United States
Devon
Reviewed August 12, 2023
Inn On Peaks Island

Find out more about Great Diamond Island

Everything you need to know about Great Diamond Island 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 Great Diamond Island 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 Great Diamond Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Great Diamond Island vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Great Diamond Island. 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 Great Diamond Island 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 $76 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 Great Diamond Island rentals

At Expedia, we put the best Great Diamond Island 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 Great Diamond 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 Great Diamond Island 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 Great Diamond 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.

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