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Top Holiday Rentals in Portland

Our top choices for Portland holiday rentals

The Fisherman's Cottage - a Lakeside Loft in the Heart of Wine Country

10.0 out of 10, Exceptional, (36)
"We had a great time!"
The price is £271
includes taxes & fees
2 Sept - 3 Sept
The Fisherman's Cottage - a Lakeside Loft in the Heart of Wine Country

Enjoy fall on the lake - colorful leaves, the grape harvest. Or, Winter snuggle.

10.0 out of 10, Exceptional, (70)
"We absolutely loved our stay and highly recommend this beautiful property. The home and amenities are exactly as described. You can’t help but have a great time. "
The price is £319
includes taxes & fees
28 Aug - 29 Aug
Enjoy fall on the lake - colorful leaves, the grape harvest. Or, Winter snuggle.

Waterfront Chautauqua Lake Home w/ Deck & Grill!

10.0 out of 10, Exceptional, (4)
"Beautiful sunsets, close to stores ,clean and comfy"
Waterfront Chautauqua Lake Home w/ Deck & Grill!

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

10.0 out of 10, Exceptional, (104)
"Great place for fishing and enjoying the lake"
Secluded Chautauqua Lake House, private dock & beach, short stroll to town!

Beautiful Wine Trail 2-BR Rental

10.0 out of 10, Exceptional, (3)
"The property was excellent, plenty of parking and super clean. The host was excellent with communications and I’ll definitely stay there again and would recommend it to anyone for a trip to Westfield or Barcelona. "
The price is £202
includes taxes & fees
4 Sept - 5 Sept
Beautiful Wine Trail 2-BR Rental

Bemus Point Vacation Rental

8.6 out of 10, Excellent, (105)
"Enjoyed the stay. Convenient and close to bemus and lake. Nice neighborhood. Would definitely stay again!"
Bemus Point Vacation Rental

Beachfront Cottage w/Amazing Views! Steps 2 Beach. Fishing.WiFi.Wineries.Dining

10.0 out of 10, Exceptional, (254)
"Our stay was absolutely amazing. We love staying at the cabin. We look forward to more stays at the lake."
Beachfront Cottage w/Amazing Views! Steps 2 Beach. Fishing.WiFi.Wineries.Dining

Cozy 3-bedroom house in charming Westfield with WiFi and all the amenities

2.0 out of 10, (5)
"We booked for this property a week ago and it took the money out of my account within 10 seconds. The day we went to the property I called the owner and they said it was not available. That was a long-term rental only we were only looking to rent it out for one day, but in my search, it came up and we took it and Now we are waiting for a refund. If it wasn’t available, it should’ve been in my search button in saying it. was very disappointed. We had to find last-minute hotel."
The price is £92
includes taxes & fees
21 Aug - 22 Aug
Cozy 3-bedroom house in charming Westfield with WiFi and all the amenities

Modern 300 ft lakefront with pool

9.6 out of 10, Exceptional, (93)
"This house was beautiful and big and roomy and perfect for all of us cousins! The host was quick to respond to any need and went above and beyond. "
Modern 300 ft lakefront with pool

Spacious 5-bedroom house with AC, WiFi in charming Bemus Point

10.0 out of 10, Exceptional, (4)
"The house was absolutely perfect and we loved the location. It was great for our group. The kitchen was so well-appointed and the grill and fire pit made our outdoor time even more enjoyable. "
Spacious 5-bedroom house with AC, WiFi in charming Bemus Point

Charming Resort in the Heart of Bemus Village on CHQ Lake

10.0 out of 10, Exceptional, (185)
"The Resort on Main was a great location for our group of five friends to get together and play games for a weekend!"
Charming Resort in the Heart of Bemus Village on CHQ Lake

Bemus Point Lake Front Cottage with Dock

9.6 out of 10, Exceptional, (81)
"Cottage and amenities were very nice. Disappointing was the several feet of muck at the lake shore which made it impossible to swim or launch a kayak from shore. The dock is unsteady and rickety; no way we could have launched a kayak from there."
Bemus Point Lake Front Cottage with Dock

Enjoy a 4-bedroom vacation home with 75 feet of lake frontage on Chautauqua Lake

10.0 out of 10, Exceptional, (178)
"Third time staying here for annual fishing trip. Obviously liked it, or wouldn’t keep coming back."
Enjoy a 4-bedroom vacation home with 75 feet of lake frontage on Chautauqua Lake

Step back in time farm house

9.6 out of 10, Exceptional, (59)
"Just me for this trip but house was immaculate will handle 2 couple easily. I really enjoyed the stay"
The price is £105
includes taxes & fees
25 Aug - 26 Aug
Step back in time farm house

Cottage #7 - Lakefront Cozy Cottage with 1 bedroom in Charming Stow, NY

8.6 out of 10, Excellent, (9)
"Perfect little cabin in a great location. Good price and have no complaints. Thank you"
Cottage #7 - Lakefront Cozy Cottage with 1 bedroom in Charming Stow, NY

Private 70ft Lakefront Cabin,3br,3ba,Pet Friendly- Kayaks/Paddle boards provided

9.8 out of 10, Exceptional, (129)
"Great place loved all the extra activity items , kayaking etc"
Private 70ft Lakefront Cabin,3br,3ba,Pet Friendly- Kayaks/Paddle boards provided

True Lake Beachfront, Stunning Sunsets, Beach glass hunting

10.0 out of 10, Exceptional, (206)
"Clean, beautiful setting, good for exploring, fishing, and relaxing. We hope to stay again. "
True Lake Beachfront, Stunning Sunsets, Beach glass hunting

Barn in Bemus Point -1 mile to Chautauqua Lake and right on the snowmobile trail

10.0 out of 10, Exceptional, (18)
"Great atmosphere and amenities!"
Barn in Bemus Point -1 mile to Chautauqua Lake and right on the snowmobile trail

Cozy Getaway ON Lake Erie

9.8 out of 10, Exceptional, (123)
"We enjoyed our visit for the week… thank you!"
Cozy Getaway ON Lake Erie

LAKEFRONT PRIVACY ON SUNSET COVE

10.0 out of 10, Exceptional, (76)
"Breathtaking views and outside space was incredible! Loved all the different spots you could sit to admire Lake Eries beauty! "
LAKEFRONT PRIVACY ON SUNSET COVE
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

Frequently asked questions

Can I find a holiday rental in Portland?

Yes, there are holiday rentals close to the most popular sights in Portland, or you can select a more secluded option if you're looking for a relaxing stay.

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

Enjoy fall on the lake - colorful leaves, the grape harvest. Or, Winter snuggle.: This holiday home rental outside of Portland is located on a lake, and has a balcony, a selection of games and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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 wider area, you’ll find 21 Brix Winery and Lily Dale Spiritual Center.

What are holiday rentals like in Portland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Portland. Holiday rentals feature amenities such as laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from shared hotel lifts and busy concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a popular option for a family trip.