Portland Holiday Rentals: Short-Term Accommodations for Rent

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

Treat yourself - Enjoy spring and summer on the lake. : 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.

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Tonight

Tomorrow

This weekend

Next weekend

Holiday Rentals in Portland

Stroll down this charming hallway, lined with a rug and featuring a convenient counter.

"Superb place "

HK$1,862 total

includes taxes & fees

11 Aug - 12 Aug

Enjoy meals in this dining area with a round table for four, surrounded by a classic wooden chair set and a large window offering a view of the lush garden.

"This was a lovely, clean property in a very quiet area. The outdoor area was beautiful and inside we had everything we needed for a great weekend visit. I’d recommend this property to anyone looking for a comfortable place to stay."

HK$1,934 total

includes taxes & fees

21 Jul - 22 Jul

Enjoy cooking in this well-equipped kitchen with an oven, microwave, and toaster.

"We wanted a place close to Peek n Peak and this was it! Great property! "

HK$1,083 total

includes taxes & fees

29 Jul - 30 Jul

Relax in a stylish living space with a flat-screen TV, fireplace, and comfortable seating area.

HK$2,607 total

includes taxes & fees

13 Aug - 14 Aug

Enjoy a serene beach experience with a rocky shoreline and calm sea.

"Stayed here for fishing trip. Nice place and Charlene is very helpful."

HK$1,890 total

includes taxes & fees

28 Jul - 29 Jul

Surrounded by lush greenery, this charming single-story home offers a peaceful retreat.

"Good place to snowmobile from"

HK$2,262 total

includes taxes & fees

28 Jul - 29 Jul

Cozy living space with a dining area, sofa, and kitchenette.

"The location is great! So convenient to get anywhere. Spotless and decorated so nice!"

HK$3,086 total

includes taxes & fees

4 Aug - 5 Aug

"Great communication with the host and a good location that was quiet and relaxing."

HK$2,776 total

includes taxes & fees

22 Jul - 23 Jul

Set amidst a serene forest, this property offers a tranquil retreat with a single-story building and a picturesque pond.

"Exceptional property! Communication was instant. One of the best properties I have ever stayed at. Had everything you could want in a stay. Property was spotless and breath taking! "

HK$7,672 total

includes taxes & fees

5 Aug - 6 Aug

Enjoy a serene view of the snowy landscape from the large window in this cozy retreat.

"We had all the aunties, uncle's and cousins for a few days of skiing. Great house, located close to Peekn Peak"

HK$5,682 total

includes taxes & fees

22 Jul - 23 Jul

Relax in this spacious room with high ceilings, a central fan, and large windows offering views of the outdoors.

"Great property !! Very clean, safe, great location, all the extras available to use for a quick weekend away!!!"

HK$2,932 total

includes taxes & fees

29 Jul - 30 Jul

Enjoy a peaceful retreat in this charming home with a backyard, picnic table, and brick pathway.

"This was one of my favorite Vrbo stays – truly unique and convenient, and incredibly spacious! I would absolutely stay there again. "

Relax by the water with comfortable wicker sofas and wooden tables under shaded umbrellas.

"Had another great stay this year. Lori was a great host. House was clean and a great location! Looking forward to our next visit!"

HK$5,020 total

includes taxes & fees

24 Jul - 25 Jul

Relax on the covered porch with comfortable seating and a stylish tile floor.

"Enjoyed our stay. Everything was as advertised. "

HK$5,002 total

includes taxes & fees

3 Aug - 4 Aug

Unwind in a serene lakeside setting with a view, a wooden deck, and a tranquil atmosphere.

"Great place to stay. Plenty of games for the kids to use.Very well stock with supply's like soap paper products ect. Great serenity."

HK$8,775 total

includes taxes & fees

30 Jul - 31 Jul

Relax with a view of the serene water from this outdoor seating area, featuring a table and comfortable chairs under a shaded canopy.

HK$4,053 total

includes taxes & fees

31 Jul - 1 Aug

Enjoy waterfront views and a serene atmosphere at this marina.

"The Resort on Main was a great location for our group of five friends to get together and play games for a weekend!"

HK$5,636 total

includes taxes & fees

22 Jul - 23 Jul

Compact kitchen area with a stove, microwave, and cabinets.

"The house is a hodgepodge of rooms very oddly added over years, I'm guessing. The only floor that didn't give when you stepped on it was the living room. Listing says they provide towels, therewere none. Listing says there's a bidet, there is not. We could hear every car that drove by. Trains every 30 minutes. Furnace kicked on repeatedly and is very loud. Steps into every other room of the house. Beds were like sleeping on cardboard. Sheets felt almost plastic. Neither of us were able to sleep....

HK$940 total

includes taxes & fees

20 Jul - 21 Jul

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Top Portland Hotel Reviews

Quality Inn

10/10 Excellent

"Room was clean. Need a few more breakfast choices that are more diabetic friendly. "

Treat yourself - Enjoy spring and summer on the lake.

10/10 Excellent

"House was as advertised. Kitchen was stocked with all the equipment you would need. Views from the deck are awesome. My family comes every year to North East, and this is one of the best houses we've stayed in. Thank you to Ethan and Melissa. "

BUTLER HOUSE at The Cherry Creek Inn

10/10 Excellent

"When I arrived at the Butler House, the owner (MK) informed me that it was actually closed for renovations. Expedia had been repeatedly informed of this but continued, nonetheless, to book reservations for guests! MK was very apologetic and offered me accommodation in the camper beside the house. It looked to be very comfortable and roomy, and had a relatively large fridge, so I accepted. Never regretted the decision. It was so quiet and cool in the evenings that I slept very soundly, and the location is totally pastoral and scenic. I thoroughly enjoyed my stay. "

Find out more about Portland

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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?

Treat yourself - Enjoy spring and summer on the lake.: 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.

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Portland Holiday Rentals

Change your mind

Treat yourself

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Holiday Rentals in Portland

The Stable at Windmill Ridge Farm

Heaven Sent - including you!

Step back in time farm house

The Refined Retreat

The Joy Of Life - Where it's all about You!

Chautauqua country home. Boat, snowmobile, fishing, wineries, family get away.

Cozy Colonial in Downtown Westfield, NY

Family & pet friendly home with yard - 5 minutes from Chautauqua Lake!

Portage Ponds 5 BR/3 Bath close to CHQ, wine trail

Spacious 5 BR Home w/ Hot Tub in Wine Country on Lake Erie

Treat yourself - Enjoy spring and summer on the lake.

Unique residence close to Chautauqua Institution.

Renovated Home in Heart of Bemus Point, Large Yard-Fire Pit- 3-4 Bedrooms

Quaint historic home in the heart of Bemus Point Village- a stroll to the water!

Beachfront Retreat in Wine Country w/ Sunset View!

LAKE VIEW. TWO MASTER BEDROOMS. PARKING. LOCATION!

Charming Resort in the Heart of Bemus Village on CHQ Lake

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

Top Portland Hotel Reviews

Quality Inn

Theater Motel

Chautauqua Harbor Hotel - Jamestown

Webb's Year Round Resort

Treat yourself - Enjoy spring and summer on the lake.

BUTLER HOUSE at The Cherry Creek Inn

Colonial Motel

Holiday Inn Express & Suites Jamestown by IHG

The White Inn

Find out more about Portland

Explore a world of travel with Expedia

Frequently asked questions