Photo by Matthew Jay

Search B&B in Middlesex

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

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Dec 26 - Dec 28
In two weeks
Jan 2 - Jan 4
In one month
Jan 16 - Jan 18
In two months
Feb 13 - Feb 15

Our top choices for Middlesex bed & breakfast

Terrace/patio
Sutherland House Victorian Bed & Breakfast

Sutherland House Victorian Bed & Breakfast

Sutherland House Victorian Bed & Breakfast
4.0 star property
Canandaigua
9.8 out of 10, Exceptional, (139)
"A wonderful time at a spectacular place. A lot of history at the Sutherland very nice place on a wonderful location "
United States
WAYNE
Sutherland House Victorian Bed & Breakfast
Sauna
The Yorkshire Inn

The Yorkshire Inn

The Yorkshire Inn
3.0 star property
Phelps
9.6 out of 10, Exceptional, (274)
"Had an amazing and relaxing time and the.breakfast in the morning was awesome "
United States
Zachary
The Yorkshire Inn
Front of property - evening/night
Los Gatos Bed & Breakfast

Los Gatos Bed & Breakfast

Los Gatos Bed & Breakfast
3.0 star property
Penn Yan
9.4 out of 10, Exceptional, (443)
"One of our best stays in Upstate New York. The property is a quaint B&B and the view in the back is amazing. The hosts are warm, friendly and just good people who treat their guests like family. The breakfasts are freshly made, the conversations full of laughter and the coffee, their special blend is just the right fuel for the day. We will definitely be going back! "
United States
Rajeshwar
Los Gatos Bed & Breakfast
Lee Suite | Premium bedding, individually decorated, individually furnished, desk
Chalet of Canandaigua

Chalet of Canandaigua

Chalet of Canandaigua
3.5 star property
Canandaigua
9.4 out of 10, Exceptional, (354)
"My daughter and i stayed here after a show at CMAC. It was lovely. "
United States
JESSICA
The price is ₩574,273
₩617,351 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Chalet of Canandaigua
Room | Premium bedding, down comforters, individually decorated
Canandaigua Guesthouse

Canandaigua Guesthouse

Canandaigua Guesthouse
4.0 star property
Canandaigua
10.0 out of 10, Exceptional, (13)
"Breakfast was wonderful as was the company. Wonderful hosts!"
United States
Mary
The price is ₩364,721
₩413,959 total
includes taxes & fees
Dec 21 - Dec 22
Canandaigua Guesthouse
Exterior
B&B at Oliver Phelps

B&B at Oliver Phelps

B&B at Oliver Phelps
4.0 star property
Canandaigua
9.2 out of 10, Wonderful, (315)
"Beautiful Inn! Karin is a gracious host and excellent tour guide Delicious breakfast each morning Great location Overall just lovely!"
United States
renee
The price is ₩317,660
₩360,552 total
includes taxes & fees
Dec 30 - Dec 31
B&B at Oliver Phelps
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 Middlesex Hotel Reviews

Holiday Inn Express Canandaigua - Finger Lakes by IHG

Holiday Inn Express Canandaigua - Finger Lakes by IHG

10/10 Excellent
"Hotel is always clean. Staff is always welcoming and the food is always great. "
Heather 1-night trip
Posted 2 days ago
Holiday Inn Express Canandaigua - Finger Lakes by IHG

Find out more about Middlesex

Middlesex B&B information

Number of reviews
638
Accommodation
12 B&B
Lowest Price
₩360,552
Highest Price
₩617,351

Frequently asked questions

Searching for B&Bs in Middlesex?
Whether you're on a romantic trip and want to stay somewhere quiet and intimate, or you're a solo traveler hoping to get some tips from locals, B&Bs can be a great choice for many types of vacationers. When you want to explore some attractions in town, Canandaigua Lake and Clarks Gully are worth a stop.
How do you know if a B&B is a good option for your stay?
Every B&B has a unique charm. Whether it's a cozy reading space or a beautiful dining room, the quaint details are what make bed and breakfasts the perfect escape.
What are the best B&Bs in Middlesex?
Here are some well-liked B&Bs in the area: Sutherland House Victorian Bed & Breakfast: 5 rooms. 11.7 mi (18.9 km) from the heart of Middlesex. Enjoy the designer toiletries and private yard. Los Gatos Bed & Breakfast: 5 rooms. Situated 10.7 mi (17.2 km) from the heart of Middlesex. Enjoy the free full breakfast and patio area. Canandaigua Guesthouse: 4 rooms. Located 13 mi (21 km) from the core of Middlesex. Enjoy the designer toiletries and fireplace in the lobby.
When should I book my B&B in Middlesex?
When you're planning your getaway to Middlesex, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 29°F. The snowiest months in Middlesex are January, March, February, and December, with each month seeing an average of 8 inches of snowfall.
What is there to do in Middlesex?
Spend some time exploring Canandaigua Lake and Clarks Gully if you're hoping to see some of the area's natural features. You might check out West River Marsh if you have time to see more of the area.

Explore a world of travel with Expedia