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Pittsfield Holiday Rentals

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    Don't let other travellers get your favourite Pittsfield area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 20 Rentals in Pittsfield
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    The following rentals are within 40 kilometres of Pittsfield.
    Chautauqua Lake Amazing Views1 / 30
    (1)Very good
    Bemus Point, NY
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Chatauqua Lake Cottage with charm1 / 54
    (2)Average
    Bemus Point, NY
    4 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Jamestown, NY
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Adorable Peak N Peek Ski/Golf Condo close to lifts and lodge, Sleeps 71 / 11
    (2)Very good
    Clymer, NY
    1 Bedroom, 2 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Wi-Fi
    • Shared Indoor Pool
    • Parking
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 October 2017
    Booked the Peak n Peek resort though RCI. Looking for a place between Cleveland, OH and Niagara Falls, NY. The two bedroom condo was clean, lots of room and full kitchen with...
    Reviewed 30 May 2017
    We were very pleased with our stay here very clean and very cute condo on one level, We came for a wedding at the peak and peak resort and This was minutes away so very...
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    About this property
    This charming condo sleeps 6 comfortably. Master bedroom has queen bed with en suite which is a full 4 piece bath. Living area holds a queen size murphy bed and a double pull out sofa. Large singe cot holds the 7th person if necessary. There is a 2nd bathroom with a shower for the guests staying...
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    Clymer, Chautauqua County 14724
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 7
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    Clarendon
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • DVD Player
    • Balcony
    • Air Conditioning
    • Terrace
    • Cable/satellite TV
    • Wi-Fi
    • Secure Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just outside of Warren, Pa. 10 Miles to The Kinzua Dam & The Allegheny Reservoir. 360 Miles of Groomed Trails for Snowmobiling Kinzua Dam for Boating. Wolf Run Marina for Docking & Restaurant. Jake's Rocks Overlook & Rimrock Trail & Overlook for Hiking & Sightseeing. Hunting in the Allegheny...
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    Clarendon, Pennsylvania 16313
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    Lakewood, NY
    1 Bedroom, 1 Bathroom, Sleeps 1 Quick View
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    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Balcony
    • Air Conditioning
    • Hot Tub
    • Washer
    • Mountain Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Hello, My name is Michele, I am the Innkeeper, I invite you to slow things down a bit and enjoy. We are the only rustic Inn located In the Chautauqua Lake area, We are located less than 1 mile from the Southern Tier Brewery, 10 min from the New National Comedy Center, 30 mins from Chautauqua and...
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    Lakewood, Chautauqua County 14750
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 1
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    Chautauqua Hillcrest Inn Jayda Room/Suite1 / 14
    (1)Excellent
    Lakewood, NY
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Private Garden
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 November 2018
    My wife and I spent the night away to check out Southern Tier Brewing. We stayed in the Jayda Room and it was perfect for what we needed! The room was comfortable, clean and the...
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    About this property
    Hello, My name is Michele, I am the Innkeeper, I invite you to slow things down a bit and enjoy. We are the only rustic Inn located In the Chautauqua Lake area, We are located less than 1 mile from the Southern Tier Brewery, 10 min from the New National Comedy Center, 30 mins from Chautauqua and...
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    Location Information
    Lakewood, Chautauqua County 14750
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Lakewood, NY
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Air Conditioning
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Hello, My name is Michele, I am the Innkeeper, I invite you to slow things down a bit and enjoy. We are the only rustic Inn located In the Chautauqua Lake area, We are located less than 1 mile from the Southern Tier Brewery, 10 min from the New National Comedy Center, 30 mins from Chautauqua and...
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    Location Information
    Lakewood, Chautauqua County 14750
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Luxury Lakeside Condo1 / 15
    (5)Very good
    Bemus Point, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • Patio
    • Housekeeping Included
    • Cable/satellite TV
    • Waterfront
    • Hot Tub
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 October 2017
    I booked Anne's condo for my wedding night and rehearsal dinner night and it was absolutely perfect! The condo is beautiful- very clean, well-decorated, spacious, and it had...
    Reviewed 29 August 2017
    Not only was the condo beautiful, clean and equipped with everything we needed but the location is amazing! We truly did not NEED to drive anywhere -- Restaurants, shopping, a...
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    About this property
    Luxury Lakeside Condo on #Chautauqua Lake direct view of the # floating stage, restaurants, shops and the Lakeside access within steps. A boat slip available and luxury accommodations . Sit on the balcony and enjoy the view or Lounge next to the pool during the open air concerts! Boating, water...
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    Location Information
    Bemus Point, Ellery 14712
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Maple Bay Get-a-Way1 / 20
    (5)Very good
    Ashville, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Porch
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    • Waterfront
    • Air Conditioning
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 August 2017
    We had a wonderful time in very nice cottage. The setting was outstanding and the unit above average for a summer cottage. I would recommend it to anyone. Rick the owner was...
    Reviewed 11 June 2017
    Average house. No towels or wash cloths wouldve been nice to know before hand. Had to go to walmart and buy some. Location was very nice. Close to jamestown was nice.
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    About this property
    Maple Bay Get-a-Way offers you the finest in private home accommodations right in the heart of the Chautauqua-Allegheny Region. Imagine walking out your back door and finding yourself just steps away from the shore of Lake Chautauqua. Sit back on the deck or under the covered porch to enjoy the...
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    Location Information
    Ashville, Chautauqua County 14710
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Lakewood, NY
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Hello, My name is Michele, I am the Innkeeper, I invite you to slow things down a bit and enjoy. We are the only rustic Inn located In the Chautauqua Lake area, We are located less than 1 mile from the Southern Tier Brewery, 10 min from the New National Comedy Center, 30 mins from Chautauqua and...
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    Location Information
    Lakewood, Chautauqua County 14750
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Stow, NY
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Patio
    • Waterfront
    • Private Garden
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Make lifelong memories when you stay at our family lakeside cottage. Enjoy the simple pleasures of living on the lake - your morning cup of coffee on the porch ,settling in with a good book, an afternoon walk to the corner ice cream shop, and roasting marshmallows by the fire. Summer the way it...
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    Stow, Chautauqua County 14785
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Eco- & Allergy Friendly Lakefront  w/Private Dock1 / 22
    (1)Very good
    Bemus Point, NY
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Washer
    • Grill
    • Patio
    • Cable/satellite TV
    • Parking
    • Wi-Fi
    • Waterfront
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 August 2016
    The key is to accept that this is a lake front cabin in a very special area. Overall it met our needs and we had a wonderful time. The two problems were a bad smeeling alge...
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    About this property
    Our cottage features a mix of vintage and mid-century modern styling while the open plan looks out to a large deck with built-in seating and to relaxing views of the Chautauqua Lake shore line and it’s surrounding rolling hills. Private dock for your boat, fishing; use our pedal boat! Short walk to...
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    Location Information
    Bemus Point, Ellery 14712
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Lakewood, NY
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Hello, My name is Michele, I am the Innkeeper, I invite you to slow things down a bit and enjoy. We are the only rustic Inn located In the Chautauqua Lake area, We are located less than 1 mile from the Southern Tier Brewery, 10 min from the New National Comedy Center, 30 mins from Chautauqua and...
    View all property information
    Location Information
    Lakewood, Chautauqua County 14750
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Lakewood, NY
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Private Garden
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    • Wi-Fi
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Hello, My name is Michele, I am the Innkeeper, I invite you to slow things down a bit and enjoy. We are the only rustic Inn located In the Chautauqua Lake area, We are located less than 1 mile from the Southern Tier Brewery, 10 min from the New National Comedy Center, 30 mins from Chautauqua and...
    View all property information
    Location Information
    Lakewood, Chautauqua County 14750
    Private Room - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Frewsburg, NY
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Parking
    • Private Garden
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Quaint Cabin near the Allegheny Mountains in both New York and Pennsylvania near the Kinzu Dam. 2 golf courses nearby by as well as boating and fishing. Not far from the Salamanca Casino. Kayak in the Allegheny River. Hike the Allegheny. No far from the Audubon near Jamestown, NY. Not far...
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    Location Information
    Frewsburg, Chautauqua County 14738
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Lakewood, NY
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Air Conditioning
    • Parking
    • Wi-Fi
    • Housekeeping Included
    • Cable/satellite TV
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Hello, My name is Michele, I am the Innkeeper, I invite you to slow things down a bit and enjoy. We are the only rustic Inn located In the Chautauqua Lake area, We are located less than 1 mile from the Southern Tier Brewery, 10 min from the New National Comedy Center, 30 mins from Chautauqua and...
    View all property information
    Location Information
    Lakewood, Chautauqua County 14750
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    New Log Cabin on Two Picturesque Trout Streams1 / 14
    (7)Very good
    Titusville
    5 Bedrooms, 3 Bathrooms, Sleeps 15 Quick View
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    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Washer
    • Grill
    • Cable/satellite TV
    • Waterfront
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 September 2017
    The very positive reviews about the beauty and condition of this cabin are true. There are, however, some negatives that need to be highlighted. I was with a group of friends...
    Reviewed 2 July 2017
    The Pennsylvania Trout House is one of the most luxurious stays you can get and in a wonderful location. It's Serene, Secluded, and very relaxing, with every amenity we'd ever...
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    About this property
    Beautiful new cedar log cabin on two acres, adjacent to two picturesque, stocked trout streams among rolling, wooded hills. Both streams stocked annually at the property line by the Penn. Fish & Boat Commission with rainbow, brown & brook trout. Cabin and adjacent guest house combined have four...
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    Location Information
    Titusville, Pennsylvania 16354
    Cabin Holiday Rental - 5 Bedrooms, 3 Bathrooms, Sleeps 15
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    Lakewood, NY
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Parking
    • Private Garden
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Hello, My name is Michele, I am the Innkeeper, I invite you to slow things down a bit and enjoy. We are the only rustic Inn located In the Chautauqua Lake area, We are located less than 1 mile from the Southern Tier Brewery, 10 min from the New National Comedy Center, 30 mins from Chautauqua and...
    View all property information
    Location Information
    Lakewood, Chautauqua County 14750
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Lakewood, NY
    1 Bedroom, 1 Bathroom, Sleeps 1 Quick View
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    Amenities & Details
    • Parking
    • Private Garden
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Hello, My name is Michele, I am the Innkeeper, I invite you to slow things down a bit and enjoy. We are the only rustic Inn located In the Chautauqua Lake area, We are located less than 1 mile from the Southern Tier Brewery, 10 min from the New National Comedy Center, 30 mins from Chautauqua and...
    View all property information
    Location Information
    Lakewood, Chautauqua County 14750
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 1
    Make Enquiry
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