Portland Vacation Rentals from ￥25,174: Search Short-Term Rentals

Q: 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.

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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

Portland

Suzanne D.

￥57,584 total

includes taxes & fees

Nov 29 - Nov 30

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

Portland

Julianne C.

￥57,584 total

includes taxes & fees

Nov 10 - Nov 11

A hot tub surrounded by trees with a wooden cabin in the background.

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

Portland

Laura

￥80,338 total

includes taxes & fees

Nov 18 - Nov 19

A modern kitchen with white cabinets, stainless steel appliances, a black countertop, and a wooden floor.

4. Beautiful Wine Trail 2-BR Rental

Westfield

Chihiro

￥40,291 total

includes taxes & fees

Nov 9 - Nov 10

A living room with a dark-colored sofa, a small side table, and a large window offering a view of trees and the sea.

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

Brocton

"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...

Christina B.

￥79,981 total

includes taxes & fees

Oct 30 - Oct 31

A modern living room with a dining table, sofa, and staircase.

6. Lake Erie Retreat

Dunkirk

Julie P.

￥31,600 total

includes taxes & fees

Nov 12 - Nov 13

A two-story house with a deck, a barbecue grill, and a sofa.

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

Chautauqua Lake

Kierstyn I.

￥39,580 total

includes taxes & fees

Nov 4 - Nov 5

A modern living room with a brick accent wall, a sofa, a bed, and a dining area.

8. Cozy Loft-Pet Friendly-Spacious

Mayville

Angela W.

￥36,055 total

includes taxes & fees

Nov 1 - Nov 2

Rear hall with bathroom and bedroom entrance.

9. The Stable at Windmill Ridge Farm

Fredonia

Jonathan M.

￥36,191 total

includes taxes & fees

Nov 3 - Nov 4

A bedroom with a bed, a desk, a chair, a ceiling fan, and a balcony with a view.

10. Premier St Elmo Unit w Large Balcony over Park

Chautauqua

Kristy C.

￥35,263 total

includes taxes & fees

Nov 2 - Nov 3

A modern kitchen with a central island, bar stools, stainless steel appliances, and pendant lighting.

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

Westfield

￥38,865 total

includes taxes & fees

Nov 29 - Nov 30

A modern kitchen with wooden chairs, a dining table, and a black cabinet.

12. Cozy Colonial in Downtown Westfield, NY

Westfield

Ken

￥55,623 total

includes taxes & fees

Nov 4 - Nov 5

A modern kitchen with white cabinetry, a dishwasher, and wooden shelves.

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

Westfield

￥50,523 total

includes taxes & fees

Nov 2 - Nov 3

A bathroom with a white sink, two mirrors, a potted plant, and patterned floor tiles.

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

Dunkirk

Ashley F.

￥51,238 total

includes taxes & fees

Nov 16 - Nov 17

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

Chautauqua

Jennifer L.

￥62,133 total

includes taxes & fees

Nov 1 - Nov 2

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

findley lake

Harry C.

￥25,174 total

includes taxes & fees

Nov 12 - Nov 13

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.

17. The Refined Retreat

Celoron

Christopher R.

￥57,540 total

includes taxes & fees

Nov 1 - Nov 2

Lakefront dining table with seating for 8 around the table

18. Casa Andante - Lakefront Escape

Mayville

Georgann F.

￥150,463 total

includes taxes & fees

Nov 1 - Nov 2

A modern kitchen with wooden cabinets, stainless steel appliances, and a granite countertop.

19. 3- Bedroom Apartment at an Award Winning Winery

Ripley

Emily Z.

￥55,267 total

includes taxes & fees

Oct 30 - Oct 31

A living room with a sofa, a coffee table, a television, and a bookshelf.

20. 3 bedrooms Cape Cod at an award wining vineyard - Sparkling Ponds Winery

Ripley

Wendy M.

￥52,505 total

includes taxes & fees

Oct 31 - Nov 1

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Top Portland Hotel Reviews

The White Inn

10/10 Excellent

"Was good."

Secluded Chautauqua Lake House, private dock & beach, short stroll to town!

10/10 Excellent

"Beautiful location. Charming, cozy, lovely home. Perfectly decorated. Immaculate. Everything we could want was already there. Well stocked kitchen. Lots of firewood, clean & well cut. Communication with host was easy with immediate response. Instructions were clear. We will be going back!"

Webb's Year Round Resort

8/10 Good

"Room was very clean and comfortable! After a long day driving and little sleep the night before the hot tub experience was a welcome delight which they let me use even though it was late at night! Need to use defoamer for hot tub, for I thought I was in an out of control bubble bath LOL. A problem when using swim suits in a hot tub! they hold a lot of soap which turns into volumes of bubbles! Can't be like Europe and be naked! The only negative was a below subpar breakfast which was very sad! Again being spoiled from traveling Europe. Would stay there again due to exceptional pricing!"

Find out more about Portland

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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.

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Check prices for these dates

Our top choices for Portland vacation rentals

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

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

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

4. Beautiful Wine Trail 2-BR Rental

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

6. Lake Erie Retreat

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

8. Cozy Loft-Pet Friendly-Spacious

9. The Stable at Windmill Ridge Farm

10. Premier St Elmo Unit w Large Balcony over Park

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

12. Cozy Colonial in Downtown Westfield, NY

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

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

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

16. Step back in time farm house

17. The Refined Retreat

18. Casa Andante - Lakefront Escape

19. 3- Bedroom Apartment at an Award Winning Winery

20. 3 bedrooms Cape Cod at an award wining vineyard - Sparkling Ponds Winery

Find vacation rentals that suit your style

Top Portland Hotel Reviews

The White Inn

Clarion Hotel Conference Center on Lake Erie

Step back in time farm house

Quality Inn Dunkirk

Best Western Dunkirk & Fredonia Inn

Holiday Inn Express & Suites Jamestown by IHG

Chautauqua Harbor Hotel - Jamestown

Secluded Chautauqua Lake House, private dock & beach, short stroll to town!

Webb's Year Round Resort

Find out more about Portland

Frequently asked questions

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