Holiday Rentals in Town of Middlebury

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Featured Holiday Rentals in Town of Middlebury

Bluebird Cottage on Silver Lake near Letchworth State Park Entrance

9.8 out of 10, Exceptional, (78)
"Jennifer is an incredible host! We were having issues with locking the door, but she came in as soon as she could to fix the door lock for us. She’s incredibly easy to contact and is always willing to go the length as a host!The house is also very clean and has a lot of appliances that make cooking easy. It’s a great property with nice outdoor seating options. "
The price is €174
includes taxes & fees
15 Jul - 16 Jul
Bluebird Cottage on Silver Lake near Letchworth State Park Entrance

Park unit #3 for rent by Silver Lake NY

9.6 out of 10, Exceptional, (19)
"It is appropriate for overnight stay and explore the area for 2 people."
The price is €181
includes taxes & fees
14 Jul - 15 Jul
Park unit #3 for rent by Silver Lake NY

The Painted Pony Cottage at LegUp Stables. Vacation with a Horse!

10.0 out of 10, Exceptional, (93)
"great location in an area with a lot of farms."
The Painted Pony Cottage at LegUp Stables. Vacation with a Horse!

Darling cottage near entrance to Letchworth State Park overlooking Silver Lake!

9.6 out of 10, Exceptional, (54)
"This is the second year my daughter and I have stayed at this cottage and we love it! It's a great space, plenty of room and super cute! The outdoor space is awesome too - grill, porch with lots of seating and fire pit area, again with lots of seating. The cottage is a short drive from lots of cool shops and restuarants too. "
The price is €141
includes taxes & fees
30 Jun - 1 Jul
Darling cottage near entrance to Letchworth State Park overlooking Silver Lake!

Lakefront Cottage with Stunning Views. Boat available to rent with cottage!

9.8 out of 10, Exceptional, (26)
"Really enjoyed Silver lake and the cottage was really nice."
Lakefront Cottage with Stunning Views. Boat available to rent with cottage!

Park model unit #5 for rent by Silver Lake NY

9.2 out of 10, Wonderful, (7)
"Everything was great! "
The price is €183
includes taxes & fees
30 Jun - 1 Jul
Park model unit #5 for rent by Silver Lake NY

Letchworth View upstairs unit on a historical site sitting on Top of the Valley!

9.6 out of 10, Exceptional, (14)
"Beautiful old farm house. Amazing property with a great view. Super clean. Would stay here again. "
Letchworth View upstairs unit on a historical site sitting on Top of the Valley!

Waterfront camper in Adirondack-like setting

9.8 out of 10, Exceptional, (28)
"Great place!"
Waterfront camper in Adirondack-like setting

Tiny Spa Cottage Retreat

9.8 out of 10, Exceptional, (87)
"Clean no bugs and quaint "
The price is €166
includes taxes & fees
5 Jul - 6 Jul
Tiny Spa Cottage Retreat

Sunrise on Conesus Lake: Pet Friendly Amazing views and blend of woods & water

9.4 out of 10, Exceptional, (13)
"We felt like we were part of your family, and the quiet surroundings were amazing! "
Sunrise on Conesus Lake: Pet Friendly Amazing views and blend of woods & water

The Shepard Farmhouse on Acreage, a Private House

9.6 out of 10, Exceptional, (41)
"Always a pleasure to stay at the Shepard house. Classic NY farm house. "
The Shepard Farmhouse on Acreage, a Private House

Park unit #4 for rent by Silver Lake NY

9.6 out of 10, Exceptional, (5)
"The stay, location, and the home were all perfect. "
The price is €182
includes taxes & fees
9 Jul - 10 Jul
Park unit #4 for rent by Silver Lake NY

The Cozy Nook! Charming 1-bedroom apartment in Batavia with WiFi, AC

The price is €132
includes taxes & fees
8 Jul - 9 Jul
The Cozy Nook! Charming 1-bedroom apartment in Batavia with WiFi, AC

Delightful, newly renovated, 3 bedroom cape in a charming country setting

2.0 star property
10.0 out of 10, Exceptional, (6)
"It was a great place to stay for a Buffalo Bills game. Go Bills!"
Delightful, newly renovated, 3 bedroom cape in a charming country setting

THE HUB -Comfy Ranch home near Letchworth-SUNY-Finger Lakes Region-Niagara Falls

2.0 star property
10.0 out of 10, Exceptional, (17)
"This house was great, clean and homie. The owners were great and if we needed anything the were right there to help. It is close to all the things that we were there to do."
The price is €322
includes taxes & fees
9 Jul - 10 Jul
THE HUB -Comfy Ranch home near Letchworth-SUNY-Finger Lakes Region-Niagara Falls

UPDATED YEAR ROUND LAKE HOUSE

10.0 out of 10, Exceptional, (57)
"Beautiful location and lots of fun things to do!"
UPDATED YEAR ROUND LAKE HOUSE

Civil War Era Home, w/King Bed, Near Conesus Lake

9.6 out of 10, Exceptional, (10)
"It's a great house, plenty of space and very clean! Perfect location, close to winery!"
Civil War Era Home, w/King Bed, Near Conesus Lake

NEW LISTING - Super 2 bedroom home with 72’ of Conesus lakefront

10.0 out of 10, Exceptional, (2)
"This was an amazing place all new appliances perfect location just a mile from the state boat launch, we brought a baby gate to keep our pets in the yard and kept our 23ft boat on the dock. The property was the most well stocked we have ever stayed at. The dock is far enough out and the depth was about 4-5 feet at the end of the dock. Bed was very comfortable views couldn’t be beat! If we had one small complaint it would be that the dock needs cleats. Perfect place for a getaway on the lake...
The price is €517
includes taxes & fees
29 Jun - 30 Jun
NEW LISTING - Super 2 bedroom home with 72’ of Conesus lakefront

Charming Village Home with an Enchanting Backyard Oasis

10.0 out of 10, Exceptional, (11)
"The location and house both exceeded our expectations! Property owner was easy to get ahold of and accommodating, would recommend this property to anyone looking to stay in Geneseo!"
Charming Village Home with an Enchanting Backyard Oasis

Amazing Sunsets! Great Yard, Parking & 1st Fl Bdrm

10.0 out of 10, Exceptional, (37)
"Excellent location and outdoor spaces. Deck and deck furniture very nice. Bathrooms outdated and tiny "
Amazing Sunsets! Great Yard, Parking & 1st Fl Bdrm
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.
Save an average of 15% on thousands of hotels when you're signed in