Photo by Matthew Jay

Search Vacation Homes in Portland

Start date: Check-in selected.
To Date
End date: Check-out

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Nov 28 - Nov 30
In two months
Jan 9 - Jan 11
In three months
Feb 6 - Feb 8
In four months
Mar 6 - Mar 8

Vacation Homes in Portland

Fridge, microwave, oven, stovetop
Peaceful, Serene, Lake View thru the trees

Peaceful, Serene, Lake View thru the trees

2.0 star property
Ashville
10.0 out of 10, Exceptional, (15)
"Clean, quiet, and cute. Couldn't ask for more."
United States
Justin M.
$243 nightly
The price is $275
Nov 13 - Nov 14
Total with taxes and fees
Peaceful, Serene, Lake View thru the trees
Fridge, microwave, oven, stovetop
Step back in time farm house

Step back in time farm house

findley lake
9.6 out of 10, Exceptional, (74)
"Great place to stay! Enjoyed the decor and location."
United States
Thomas B.
$133 nightly
The price is $150
Nov 24 - Nov 25
Total with taxes and fees
Step back in time farm house
Smart TV, fireplace, books
The Refined Retreat

The Refined Retreat

Celoron
10.0 out of 10, Exceptional, (12)
"We really couldn't have asked for more. Top notch clean and comfortable. More amenities than you can imagine. Quiet neighborhood. Instant communication with owners. Ample space. Would highly recommend!"
United States
jessica w.
$265 nightly
The price is $300
Nov 11 - Nov 12
Total with taxes and fees
The Refined Retreat
Terrace/patio
Lakefront w Dock, Pet Friendly, Spacious Yard

Lakefront w Dock, Pet Friendly, Spacious Yard

2.0 star property
Chautauqua Lake
9.8 out of 10, Exceptional, (13)
"This was a great property to stay at! I couldn’t have asked for anything different. What stood out the most was how clean everything was and how friendly the host was; all our questions were answered promptly and the host was exceedingly helpful. Overall great place to stay!"
United States
Melissa C.
$230 nightly
The price is $260
Nov 11 - Nov 12
Total with taxes and fees
Lakefront w Dock, Pet Friendly, Spacious Yard
Property grounds
Chautauqua country home. Boat, snowmobile, fishing, wineries, family get away.

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

Dewittville
10.0 out of 10, Exceptional, (57)
"Great place! Stayed for a night after a concert at Chautauqua. Had all the amenities we needed and excellent layout to accommodate all of us. We couldn't have asked for more!"
United States
Cheryl T.
$246 nightly
The price is $278
Nov 11 - Nov 12
Total with taxes and fees
Chautauqua country home. Boat, snowmobile, fishing, wineries, family get away.
Marina
Charming Resort in the Heart of Bemus Village on CHQ Lake

Charming Resort in the Heart of Bemus Village on CHQ Lake

Bemus Point
10.0 out of 10, Exceptional, (195)
"This property was amazing! Plenty of space, very clean, and within walking distance of shops and restaurants in Bemus Point and also very close to the lake. The property has an excellent layout, wonderful side and front porches, and is kid friendly. I would highly recommend and we will be staying there again in the future!"
United States
Zackary F.
$447 nightly
The price is $505
Nov 11 - Nov 12
Total with taxes and fees
Charming Resort in the Heart of Bemus Village on CHQ Lake
Interior
The Stable at Windmill Ridge Farm

The Stable at Windmill Ridge Farm

Fredonia
9.6 out of 10, Exceptional, (14)
"Superb place "
Canada
Jonathan M.
$192 nightly
The price is $217
Nov 11 - Nov 12
Total with taxes and fees
The Stable at Windmill Ridge Farm
3 bedrooms, iron/ironing board, WiFi, bed sheets
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, (1)
"It was a very clean house with spacious areas including a full apartment upstairs. It was one of the better places we have ever stayed at as far as accommodations go. Highly recommended! Thank you."
United Kingdom
Bill T.
$366 nightly
The price is $414
Nov 14 - Nov 15
Total with taxes and fees
20 Park-Walk to Everything CHQ-Pets OK-Free Bikes
Exterior
Perfect Fall getaway! Leaves, Wine Tasting, Fishing, Birding, Family Time!

Perfect Fall getaway! Leaves, Wine Tasting, Fishing, Birding, Family Time!

Mayville
9.8 out of 10, Exceptional, (23)
"Our stay was amazing from start to finish. Property was absolutely stunning, family friendly, very clean, cozy, and well equipped. Patti and Rich have thought of every little detail to make this house a home and to make you feel welcome we will definitely be coming back over the summer and to ski next winter! "
United States
Rachael W.
$360 nightly
The price is $407
Nov 18 - Nov 19
Total with taxes and fees
Perfect Fall getaway! Leaves, Wine Tasting, Fishing, Birding, Family Time!
Exterior
Portage Ponds 5 BR/3 Bath close to CHQ, wine trail

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

Westfield
10.0 out of 10, Exceptional, (22)
"We had a fantastic stay at this property. Plenty of creature comforts to make it a home away from home. Tiffany was great. The location was perfect. I would stay at this property again. "
United Kingdom
Allen E.
$615 nightly
The price is $695
Nov 11 - Nov 12
Total with taxes and fees
Portage Ponds 5 BR/3 Bath close to CHQ, wine trail
Interior
Walk out the door, walk onto the beach!

Walk out the door, walk onto the beach!

Dunkirk
10.0 out of 10, Exceptional, (75)
"My wife and family stayed here. We grew up in this area and could not have found a better place to stay. Everything was perfect!"
United States
Kevin K.
$422 nightly
The price is $477
Nov 17 - Nov 18
Total with taxes and fees
Walk out the door, walk onto the beach!
Fridge, microwave, oven, stovetop
Main St Bemus-HOT TUB-1 Block from Lake

Main St Bemus-HOT TUB-1 Block from Lake

Ellery
10.0 out of 10, Exceptional, (7)
"Enjoyed the property and our stay in Bemus Point. The home was clean and comfortable. Plenty of space for multiple families. We enjoyed the firepit several nights and the smores bar was a special treat. The home is walkable to Bemus Point restaurants and shops. We would highly recommend staying at this home and we hope to return in the near future. "
United States
Bart C.
$449 nightly
The price is $507
Nov 11 - Nov 12
Total with taxes and fees
Main St Bemus-HOT TUB-1 Block from Lake
Smart TV, books
Cozy Colonial in Downtown Westfield, NY

Cozy Colonial in Downtown Westfield, NY

Westfield
10.0 out of 10, Exceptional, (23)
"Great property in the perfect location. Very clean, updated property. We will definitely stay again. "
United States
Marci S.
$309 nightly
The price is $349
Nov 30 - Dec 1
Total with taxes and fees
Cozy Colonial in Downtown Westfield, NY
Property grounds
LAKE VIEW. TWO MASTER BEDROOMS. PARKING. LOCATION!

LAKE VIEW. TWO MASTER BEDROOMS. PARKING. LOCATION!

Chautauqua
$457 nightly
The price is $516
Nov 13 - Nov 14
Total with taxes and fees
LAKE VIEW. TWO MASTER BEDROOMS. PARKING. LOCATION!
Interior
Spacious 5 BR Home w/ Hot Tub in Wine Country on Lake Erie

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

North East
9.6 out of 10, Exceptional, (20)
"Very nice and spacious house. "
United States
Larry M.
$601 nightly
The price is $674
Nov 18 - Nov 19
Total with taxes and fees
Spacious 5 BR Home w/ Hot Tub in Wine Country on Lake Erie
Terrace/patio
Fall Fun on the Lake - 180 degree Views

Fall Fun on the Lake - 180 degree Views

2.0 star property
North East
10.0 out of 10, Exceptional, (5)
"Great house, very clean, great communication with Mark. Would stay again if we’re in the area!"
United States
Anthony C.
$766 nightly
The price is $859
Nov 11 - Nov 12
Total with taxes and fees
Fall Fun on the Lake - 180 degree Views
Outdoor dining
Casa Andante - Lakefront Escape

Casa Andante - Lakefront Escape

Mayville
10.0 out of 10, Exceptional, (64)
"We really enjoyed our stay! The view was beautiful. Appreciated all of the bedrooms and full baths."
United States
Mary L.
$827 nightly
The price is $934
Nov 12 - Nov 13
Total with taxes and fees
Casa Andante - Lakefront Escape
Property grounds
Beachfront Retreat in Wine Country w/ Sunset View!

Beachfront Retreat in Wine Country w/ Sunset View!

2.0 star property
North East
10.0 out of 10, Exceptional, (13)
"House was perfect for our family. Good sized rooms for parents with children, great spaces to gather and have fun. Outside areas afforded plenty of safe yards to run and play. "
United States
Steven M.
$800 nightly
The price is $830
Nov 18 - Nov 19
Total with taxes and fees
Beachfront Retreat in Wine Country w/ Sunset View!
Private kitchen
Cozy 3-bedroom house in charming Westfield with WiFi and all the amenities

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

Westfield
2.0 out of 10, (6)
"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....
United States
Miranda
$106 nightly
The price is $120
Nov 11 - Nov 12
Total with taxes and fees
Cozy 3-bedroom house in charming Westfield with WiFi and all the amenities
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Portland Hotel Reviews

Chautauqua Harbor Hotel - Jamestown

Chautauqua Harbor Hotel - Jamestown

10/10 Excellent
"Friendliness of staff."
Carl 2-night trip
Posted 2 days ago
Chautauqua Harbor Hotel - Jamestown

Find out more about Portland

Portland Vacation Homes information

Number of reviews
628
Accommodation
178 Vacation Homes
Lowest Price
$120
Highest Price
$934

Explore a world of travel with Expedia