A large suspension bridge with a distinctive gothic arch design, spanning over a forested area.

Portland Vacation Rentals

Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Portland vacation rentals

A spiral staircase with wooden steps and metal railings, leading to an upper level with a skylight.

1. Cozy Lake-View Cottage for 4 · Wine Tasting Included · Pet Friendly

Cozy Lake-View Cottage for 4 · Wine Tasting Included · Pet Friendly
Portland
10.0 out of 10, Exceptional, (65 reviews)
"Loved our stay! Will stay again!"
United States
Dustin T.
$323 nightly
The price is $365
Oct 25 - Oct 26
Total with taxes and fees
Cozy Lake-View Cottage for 4 · Wine Tasting Included · Pet Friendly
A modern kitchen with dark cabinetry, a central island, and a dining area with a chair and table.

2. Charming 2BR Cottage · Near Lake Lookout · Wine Tasting Included · Pet Friendly

Charming 2BR Cottage · Near Lake Lookout · Wine Tasting Included · Pet Friendly
Portland
9.6 out of 10, Exceptional, (7 reviews)
"Cute cottage. Perfect location. Very clean and the process was very smooth."
United States
Julianne C.
$323 nightly
The price is $365
Oct 25 - Oct 26
Total with taxes and fees
Charming 2BR Cottage · Near Lake Lookout · Wine Tasting Included · Pet Friendly
A forest with a fire pit surrounded by Adirondack chairs.

3. Modern Lux Tiny Cabins in Wooded Getaway w/Hot Tub

Modern Lux Tiny Cabins in Wooded Getaway w/Hot Tub
Portland
10.0 out of 10, Exceptional, (1 review)
"Beautiful setting near Lake Erie and hiking trails. Fun design, great for families/small groups. Bring your own drinking water though if you mind sulfer."
United States
Laura
$445 nightly
The price is $503
Nov 2 - Nov 3
Total with taxes and fees
Modern Lux Tiny Cabins in Wooded Getaway w/Hot Tub
A living room with a dark-colored sofa, a small side table, and a large window offering a view of trees and the sea.

4. Lakefront Cottage with Spectacular Lake Erie Views near boat launch

Lakefront Cottage with Spectacular Lake Erie Views near boat launch
Brocton
10.0 out of 10, Exceptional, (4 reviews)
"My husband and I were looking for a quiet escape, and this charming cottage on Lake Erie delivered in every way. The lake views alone are worth the stay. We couldn't stop staring at the water from the moment we arrived.The space is clean, cozy, and thoughtfully put together. Comfy beds and pillows. The updated bathroom was a nice surprise, and the kitchen had everything we needed!Our favorite moment? Sitting by the fire pit at sunset with our two Yorkies, watching the sky turn pink and orange...
United States
Christina B.
$448 nightly
The price is $506
Oct 23 - Oct 24
Total with taxes and fees
Lakefront Cottage with Spectacular Lake Erie Views near boat launch
A two-story house with a front porch, a black door, and a small garden area with potted plants.

5. Beautiful Wine Trail 2-BR Rental

Beautiful Wine Trail 2-BR Rental
Westfield
9.8 out of 10, Exceptional, (18 reviews)
"You have the whole house so it is nice and quiet. I stayed here twice this summer and it was very convenient and relaxing. AC works well and the bed is comfortable."
United States
Chihiro
$228 nightly
The price is $258
Nov 16 - Nov 17
Total with taxes and fees
Beautiful Wine Trail 2-BR Rental
A modern living room with a dining table, sofa, and staircase.

6. Lake Erie Retreat

Lake Erie Retreat
Dunkirk
10.0 out of 10, Exceptional, (4 reviews)
"Great little place. We loved our short stay."
United States
Julie P.
$178 nightly
The price is $201
Oct 27 - Oct 28
Total with taxes and fees
Lake Erie Retreat
A two-story house with a deck, a barbecue grill, and a sofa.

7. Lakefront w Dock-Pets OK-Amazing Views-Large Deck

Lakefront w Dock-Pets OK-Amazing Views-Large Deck
Chautauqua Lake
9.8 out of 10, Exceptional, (19 reviews)
"Beautiful views of the lake and a nice little place to stay!"
United States
Kierstyn I.
$221 nightly
The price is $250
Oct 26 - Oct 27
Total with taxes and fees
Lakefront w Dock-Pets OK-Amazing Views-Large Deck
A modern living room with a brick accent wall, a sofa, a bed, and a dining area.

8. Cozy Loft-Pet Friendly-Spacious

Cozy Loft-Pet Friendly-Spacious
Mayville
10.0 out of 10, Exceptional, (4 reviews)
"Great stay. Clean loft and pet friendly.Host was easy to"
United States
Angela W.
$207 nightly
The price is $234
Nov 1 - Nov 2
Total with taxes and fees
Cozy Loft-Pet Friendly-Spacious
A laundry room with a white washing machine and dryer, a white cabinet with drawers, and a floral-patterned wall.

9. Stay on Main: Stylish loft in heart of the village

Stay on Main: Stylish loft in heart of the village
Westfield
$218 nightly
The price is $246
Oct 25 - Oct 26
Total with taxes and fees
Stay on Main: Stylish loft in heart of the village
Room

10. Spacious 3BR Home with Pool Table & Patio Near Lake Erie

Spacious 3BR Home with Pool Table & Patio Near Lake Erie
Westfield
$283 nightly
The price is $320
Nov 2 - Nov 3
Total with taxes and fees
Spacious 3BR Home with Pool Table & Patio Near Lake Erie
A modern kitchen with wooden chairs, a dining table, and a black cabinet.

11. Cozy Colonial in Downtown Westfield, NY

Cozy Colonial in Downtown Westfield, NY
Westfield
10.0 out of 10, Exceptional, (32 reviews)
"Great clean place in a good part of town so we were able to walk to the bars and restaurants in a few minutes. Will for sure book this same place next year when we are up on fishing trip and wine arounds."
United States
Ken
$311 nightly
The price is $351
Oct 24 - Oct 25
Total with taxes and fees
Cozy Colonial in Downtown Westfield, NY
A living room with a stone fireplace, a television, and a dining area in the background.

12. Walk out the door, walk onto the beach!

Walk out the door, walk onto the beach!
Dunkirk
10.0 out of 10, Exceptional, (99 reviews)
"Beautiful property and super nice host!"
United States
Ashley F.
$287 nightly
The price is $324
Nov 16 - Nov 17
Total with taxes and fees
Walk out the door, walk onto the beach!
A bedroom with a bed, a desk, a chair, a ceiling fan, and a balcony with a view.

13. Premier St Elmo Unit w Large Balcony over Park

Premier St Elmo Unit w Large Balcony over Park
Chautauqua
10.0 out of 10, Exceptional, (2 reviews)
"This unit was perfect and just as described in the listing. The owners were very good with communication and helping us be prepared for our trip."
United States
Kristy C.
$198 nightly
The price is $220
Nov 1 - Nov 2
Total with taxes and fees
Premier St Elmo Unit w Large Balcony over Park
A timer makes sure your entry is lighted for evening arrivals.

14. The Stable at Windmill Ridge Farm

The Stable at Windmill Ridge Farm
Fredonia
9.6 out of 10, Exceptional, (18 reviews)
"Superb place "
Canada
Jonathan M.
$189 nightly
The price is $214
Oct 25 - Oct 26
Total with taxes and fees
The Stable at Windmill Ridge Farm
A single-story house with a front porch, a small garden, and a driveway.

15. 20 Park-Walk to Everything CHQ-Pets OK-Free Bikes

20 Park-Walk to Everything CHQ-Pets OK-Free Bikes
Chautauqua
10.0 out of 10, Exceptional, (8 reviews)
"Great property. Tiffany thought of everything. It was all so welcoming and new. Would definitely stay here again. "
United States
Jennifer L.
$399 nightly
The price is $451
Oct 25 - Oct 26
Total with taxes and fees
20 Park-Walk to Everything CHQ-Pets OK-Free Bikes
A kitchen with a central island, bar stools, a hanging light fixture, and a painting on the wall.

16. Step back in time farm house

Step back in time farm house
findley lake
9.6 out of 10, Exceptional, (102 reviews)
"Our second stay at this property, awesome we will be back"
United States
Harry C.
$133 nightly
The price is $150
Nov 2 - Nov 3
Total with taxes and fees
Step back in time farm house
Spacious patio with outdoor kitchen

17. Casa Andante - Lakefront Escape

Casa Andante - Lakefront Escape
Mayville
10.0 out of 10, Exceptional, (70 reviews)
"Our family celebrated a beautiful weekend at Casa Adante. The property provided everything we needed, easy check in, serene lake views, proximity to cool places around the lake, and plenty of space. Thank you to the hosts for creating a cozy place where amazing memories were made! "
United States
Georgann F.
$859 nightly
The price is $971
Oct 27 - Oct 28
Total with taxes and fees
Casa Andante - Lakefront Escape
A modern kitchen with a central island, stainless steel appliances, and bar stools.

18. Cozy 2-bedroom condo in beautiful Chautauqua Institution

Cozy 2-bedroom condo in beautiful Chautauqua Institution
Chautauqua
$400 nightly
The price is $452
Oct 23 - Oct 24
Total with taxes and fees
Cozy 2-bedroom condo in beautiful Chautauqua Institution
A modern interior with a living area, kitchen, and dining space, featuring wooden beams, large windows, and a flat-screen TV.

19. Quiet Escape, Peaceful Lake Glimpses

Quiet Escape, Peaceful Lake Glimpses
Ashville
10.0 out of 10, Exceptional, (24 reviews)
"Beautiful location! We enjoyed the peaceful quiet time."
United States
Anonymous traveler
$297 nightly
The price is $328
Oct 25 - Oct 26
Total with taxes and fees
Quiet Escape, Peaceful Lake Glimpses
A modern living room with a fireplace, a flat-screen TV, a dining area with a table and chairs, and a kitchen with wooden cabinets and a refrigerator.

20. The Refined Retreat

The Refined Retreat
Celoron
9.8 out of 10, Exceptional, (27 reviews)
" wonderful place to stay "
United States
Christopher R.
$323 nightly
The price is $365
Oct 25 - Oct 26
Total with taxes and fees
The Refined Retreat
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 Portland Hotel Reviews

The White Inn

The White Inn

10/10 Excellent
"Hotel was excellent will stay there again"
Mark 1-night trip
Posted 2 hours ago
The White Inn

Find out more about Portland

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

Portland vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Portland. 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 Portland 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 $150 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 Portland rentals

At Expedia, we put the best Portland 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 Portland 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 Portland 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 Portland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Portland?

Yes, there are vacation rentals close to popular attractions in Portland, or you can select a more remote option if you want a relaxing place to stay.

What are some of the best vacation home rentals that Portland has to offer?

Beautiful Pet friendly cottage by the Stow Ferry: This vacation home rental outside of Portland is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

What can I see and do in Portland?

While exploring the area, visit family-friendly sights like Chautauqua Belle Steamboat, or get outside and enjoy nature at Lake Erie. In the larger area, you’ll find 21 Brix Winery and Lake Erie State Park.

What are vacation rentals like in Portland?

Vacation rentals are private properties you can reserve for a couple days or more in Portland. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so your stay will be comfortable. If you're concerned about cleanliness, a vacation rental can provide a sense of security away from shared hotel elevators and busy reception areas while still allowing you to travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for family trips.