The 10 best holiday rentals in Middlesex, USA | Booking.com
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Holiday Rentals in Middlesex

Find the holiday rentals that appeal to you the most

The best holiday rentals in Middlesex

Check out our pick of great holiday rentals in Middlesex

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Sutherland House Victorian Bed and Breakfast

Canandaigua (Near Middlesex)

Boasting a garden and views of garden, Sutherland House Victorian Bed and Breakfast is a bed and breakfast set in a historic building in Canandaigua, 4.6 km from Sonnenberg Gardens Mansion State...

M
Mahala
From
Spain
it was a lovely stay, the owners are really nice people. we had a wonderful night and great breakfast. deeply recommend! thank you so much!
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 101 reviews
Price from
US$142.80
1 night, 2 adults

Italy Hill Estate

Branchport (Near Middlesex)

Boasting a hot tub, Italy Hill Estate is situated in Branchport. Guests can benefit from a patio and a children's playground. The property features a restaurant with an outdoor dining area.

Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 7 reviews
Price from
US$353
1 night, 2 adults

Los Gatos Bed & Breakfast

Penn Yan (Near Middlesex)

Los Gatos Bed & Breakfast in Penn Yan provides adults-only accommodation with a garden and a shared lounge. This property offers access to a patio and free private parking.

J
Joyce
From
United States
Beautiful location. Rebecca and Charlie made everything very comfortable and were exceptionally gracious. Fantastic stay!
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 59 reviews
Price from
US$189
1 night, 2 adults

Heated & AC Full Bathroom Covered Wagon

Penn Yan (Near Middlesex)

Located 39 km from Watkins Glen International, 27 km from Finger Lakes Boating Museum and 40 km from Hobart And William Smith Colleges, Heated & AC Full Bathroom Covered Wagon offers accommodation...

T
Theresa
From
Canada
Wagon was everything n more we could of asked for. Lots of thought put into the decor. Quietness of the area, even the early morning rooster didn't bother us. It actually added to the feel. Bonfire was great. BONUS, we were able to get a good amount of firewood right at the beginning of our road for a better deal then elsewhere.
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 49 reviews
Price from
US$110.40
1 night, 2 adults

Heated & AC Yurt

Penn Yan (Near Middlesex)

Situated 24 km from Glenn H Curtiss Museum, Heated & AC Yurt features accommodation with free WiFi and free private parking.

K
Karim
From
United Kingdom
Perfect antidote to city life, perfectly presented in a great location. Wished we could have stayed longer.
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 11 reviews
Price from
US$123.05
1 night, 2 adults

Rustic Ridge

Penn Yan (Near Middlesex)

Rustic Ridge is situated in Penn Yan, 39 km from Watkins Glen International, 27 km from Finger Lakes Boating Museum, as well as 41 km from Hobart And William Smith Colleges.

S
Subhendu
From
United States
The location which is totally off the grid, perfect for a couples hideout. The cottage itself is very neat. Has a fully functioning fireplace, basic solar powered electricity and lighting. Outside seating arrangement, fire pit. Moderately comfortable 3 beds that can take four adults at max. It is definitely recommended for couples of group of friends looking for an adventure stay.
Scored out of 10, guest rating 6.8
Pleasant - What previous guests thought, 13 reviews
Price from
US$78.20
1 night, 2 adults

Lakeside Condo with plenty of amenities close to Bristol Mountain - permit - 2024-0018

Canandaigua (Near Middlesex)

Set in Canandaigua, 20 km from Sonnenberg Gardens Mansion State Historic Park and 23 km from Cmac Performing Arts Center, Lakeside Condo with plenty of amenities close to Bristol Mountain - permit -...

Scored out of 10, guest rating 8.4
Very good - What previous guests thought, 10 reviews

Cozy Family Home

Penn Yan (Near Middlesex)

Cozy Family Home is situated in Penn Yan, 39 km from Glenn H Curtiss Museum, 40 km from Sonnenberg Gardens Mansion State Historic Park, as well as 43 km from Women'S Rights National Historical Park.

Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 5 reviews

Country Cottage

Penn Yan (Near Middlesex)

Situated in Penn Yan, 32 km from Glenn H Curtiss Museum and 50 km from Sonnenberg Gardens Mansion State Historic Park, Country Cottage offers a garden and air conditioning.

M
Maya
From
United States
This cottage is amazing, it is fully equipped, includes a deck with grill, a screened porch, and is situated midst in a large surroundings with garden, lawn and trees. An absolute highlight is the house's own pond where you walk around or sit in the adirondack chairs to see and hear frogs, watch bunnies jumping around and grazing, and observe birds. This rental and its setting is quiet and beautiful, just a dream. The cottage is at the Keuka lake and 10' from Penn Yan, with shopping, wine tasting locations, restaurants, boat renting and more. The location is a short drive from Watkins Glen State Park with its 19 waterfalls, other natural wonders and lakes, and about 1hr drive from the wonderful Corning Museum of Glass. what else can you dream of for a relaxing vacation.
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 11 reviews

Charming Stanley Home with Yard, 7 Mi to Seneca Lake

Geneva (Near Middlesex)

Charming Stanley Home with Yard, 7 Mi to Seneca Lake is situated in Geneva, 32 km from Women'S Rights National Historical Park, 14 km from Hobart And William Smith Colleges, and 17 km from Cmac...

Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 14 reviews
All holiday rentals in Middlesex