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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Compare 33 B&B in Middletown with updated reviews, rates, and availability.

The Bergson
Lobby lounge

The Bergson

3.0 star property
9.0 out of 10, Wonderful, (933)
"Great stay"
The Bergson
The Ruse
Exterior

The Ruse

5.0 star property
9.6 out of 10, Exceptional, (77)
"The most absolute amazing place to enjoy the perfect weekend getsway"
The price is AED 1,307
AED 1,519 total
includes taxes & fees
4 May - 5 May
The Ruse
Camellia Inn
Lobby

Camellia Inn

3.5 star property
8.4 out of 10, Very Good, (574)
"Great stay. Friendly staff and wonderful room.close to the square, you can walk everywhere.Wine tasting at affiliated wineries is included. Parking n back is a little tight but plenty of street parking. Definitely will be back "
The price is AED 1,232
AED 1,429 total
includes taxes & fees
18 May - 19 May
Camellia Inn
Healdsburg Inn on the Plaza, A Four Sisters Inn
Front of property

Healdsburg Inn on the Plaza, A Four Sisters Inn

3.5 star property
8.6 out of 10, Excellent, (550)
"Perfect location, nice staff, comfortable rooms and breakfast. We will stay here again! "
The price is AED 989
AED 1,150 total
includes taxes & fees
11 May - 12 May
Healdsburg Inn on the Plaza, A Four Sisters Inn
Calistoga Wine Way Inn
Terrace/patio

Calistoga Wine Way Inn

3.0 star property
8.6 out of 10, Excellent, (581)
"Love to stay here again "
The price is AED 601
AED 692 total
includes taxes & fees
5 May - 6 May
Calistoga Wine Way Inn
Grape Leaf Inn
Suite | Balcony

Grape Leaf Inn

4.0 star property
9.4 out of 10, Exceptional, (153)
"A cute, vintage b&b near the square! Such nice hosts, and a delicious breakfast! "
The price is AED 1,227
AED 1,423 total
includes taxes & fees
4 May - 5 May
Grape Leaf Inn
Featherbed Railroad B&B Resort
Fishing

Featherbed Railroad B&B Resort

3.0 star property
9.0 out of 10, Wonderful, (386)
"The stay in the rooms of the trains were beautiful, cozy nice and clean will tell friends and family. The staff members were great."
Featherbed Railroad B&B Resort
Wine Country Inn & Cottages Napa Valley
Front of property

Wine Country Inn & Cottages Napa Valley

4.0 star property
9.0 out of 10, Wonderful, (704)
"Beautiful surroundings, stunning location, delicious breakfast, extremely comfortable room and balcony area."
Wine Country Inn & Cottages Napa Valley
Craftsman Inn
Individually decorated, individually furnished, iron/ironing board

Craftsman Inn

3.5 star property
9.0 out of 10, Wonderful, (244)
"Good value Inn, well maintained and nicely appointed "
The price is AED 807
AED 929 total
includes taxes & fees
6 May - 7 May
Craftsman Inn
Chateau De Vie
Exterior

Chateau De Vie

3.0 star property
9.8 out of 10, Exceptional, (40)
"Serene and quiet location. Excellent staff! Wonderful breakfast. Bathroom is small"
The price is AED 1,621
AED 1,864 total
includes taxes & fees
12 May - 13 May
Chateau De Vie
Bed & Barrel at Stonehouse Cellars
Outdoor spa tub

Bed & Barrel at Stonehouse Cellars

4.0 star property
9.4 out of 10, Exceptional, (53)
"Excellent stay- hidden gem"
The price is AED 826
AED 921 total
includes taxes & fees
1 Jun - 2 Jun
Bed & Barrel at Stonehouse Cellars
Inn St Helena
Deluxe Studio | View from room

Inn St Helena

3.0 star property
9.4 out of 10, Exceptional, (147)
"This is the best place fo stay next time "
The price is AED 1,166
AED 1,341 total
includes taxes & fees
4 May - 5 May
Inn St Helena
Embrace Calistoga
Front of property - evening/night

Embrace Calistoga

3.5 star property
10.0 out of 10, Exceptional, (47)
"Great hosts Chris and Brett very hospitable & professional. Clean and well appointed rooms. One of the best places we stayed at. Noelleen & Michael "
The price is AED 1,062
AED 1,221 total
includes taxes & fees
4 May - 5 May
Embrace Calistoga
Pinschower Inn
Terrace/patio

Pinschower Inn

3.5 star property
9.8 out of 10, Exceptional, (27)
"Alison was wonderful and made the best breakfast ever! We loved the history of the inn"
Pinschower Inn
Bear Flag Inn
Property entrance

Bear Flag Inn

3.0 star property
9.6 out of 10, Exceptional, (117)
"The hosts were very hospitable, and the breakfasts were amazing!"
The price is AED 915
AED 1,052 total
includes taxes & fees
4 May - 5 May
Bear Flag Inn
Potter's Foothill House
Palisade Cottage | Individually decorated, individually furnished, desk, iron/ironing board

Potter's Foothill House

3.5 star property
10.0 out of 10, Exceptional, (24)
"Had a great stay at Potter’s Foothill House. We stayed in the Palisades cottage, which was a quiet, private spot on the beautiful property. Breakfasts were amazing every morning! Highly recommend!!!"
The price is AED 1,212
AED 1,394 total
includes taxes & fees
11 May - 12 May
Potter's Foothill House
RustRidge Bed and Breakfast - Poolside Room
Terrace/patio

RustRidge Bed and Breakfast - Poolside Room

9.6 out of 10, Exceptional, (7)
"Susan and Jim seemed like old friends by the end of our stay. We want to come back in the summer! A beautiful property!"
RustRidge Bed and Breakfast - Poolside Room
The River Belle Inn
Exterior

The River Belle Inn

3.5 star property
10.0 out of 10, Exceptional, (133)
"charm, service, comfort - what a total joy to stay at this inn! "
The River Belle Inn
My Big Art Project
Exterior

My Big Art Project

3.5 star property
9.8 out of 10, Exceptional, (19)
"We very much enjoyed our stay! As fellow creatives, it was fun to be immersed in a Big Art Project that we learned about during the home gallery tour. It was the perfect place to spend the night with our local friends nearby. The hummingbirds and fish in the pond entertained us out of our bedroom window. "
The price is AED 686
AED 796 total
includes taxes & fees
5 May - 6 May
My Big Art Project
Thorn Hill Vineyard Villas
Basic Room | Premium bedding, individually decorated, individually furnished

Thorn Hill Vineyard Villas

3.5 star property
9.0 out of 10, Wonderful, (16)
"My suite was very nice and quiet. I enjoyed the shared living area and full kitchen. The bath was very nice and included a handheld shower which is rare. "
The price is AED 757
AED 844 total
includes taxes & fees
4 May - 5 May
Thorn Hill Vineyard Villas
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.
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Other property types in Middletown

Backyard Garden Oasis
Deep-tissue massages, Swedish massages, prenatal massages, massages

Backyard Garden Oasis

3.0 star property
9.6 out of 10, Exceptional, (44)
"perfect place"
The price is AED 713
AED 795 total
includes taxes & fees
4 May - 5 May
Backyard Garden Oasis
Calistoga Creek Side Mountain Estate
A heated pool

Calistoga Creek Side Mountain Estate

9.6 out of 10, Exceptional, (4)
"Absolutely perfect for our work retreat! Such a gem of a place."
Calistoga Creek Side Mountain Estate
Clear Lake Cottages & Marina
View from property

Clear Lake Cottages & Marina

2.5 star property
9.0 out of 10, Wonderful, (303)
"Great stay!"
The price is AED 537
AED 599 total
includes taxes & fees
19 May - 20 May
Clear Lake Cottages & Marina
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.

Frequently asked questions

Searching for B&Bs in Middletown?
If you want to find a place to stay with fewer rooms than a hotel and an intimate environment, a B&B may be the perfect thing for your vacation to Middletown. If your ideal vacation to Middletown includes spending lots of time outside, Boggs Mountain Demonstration State Forest is a good spot to enjoy the scenery.
Why should you consider B&Bs instead of traditional hotels?
B&Bs all have a unique charm. Whether it’s a garden for guests to admire or a sunlit breakfast nook to enjoy your morning cup of coffee, the little details are what make bed and breakfasts a home away from home.
What are the best B&Bs in Middletown?
Below are some well-liked B&Bs in the area: The Bergson: 22 rooms. 12.4 mi (20 km) from the heart of Middletown. Enjoy the unique décor and fireplace in the lobby. Chateau De Vie: 5 rooms. 11 mi (17.6 km) from the downtown core. Enjoy the local cuisine breakfast and private yard. Calistoga Wine Way Inn: 8 rooms. Situated 12.4 mi (20 km) from the heart of Middletown. Enjoy the local cuisine breakfast and designer toiletries. The Ruse: 11 rooms. 16.9 mi (27.2 km) from the heart of downtown. Enjoy the free cooked breakfast and designer toiletries. Healdsburg Inn on the Plaza, A Four Sisters Inn: 12 rooms. Located 16.9 mi (27.2 km) from the core of Middletown. Enjoy the massage services and fireplace in the lobby.
What's the best time of year to book my B&B in Middletown?
When you’re dreaming of a trip to Middletown, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 70°F, while the coldest months are December and January with an average of 48°F. Average annual precipitation for Middletown is 26 inches.
What is there to do in Middletown?
If you’re looking for some activities to entertain you on your trip, consider visiting Beaver Creek Vineyards and Langtry Estate and Vineyards. You might put Twin Pine Casino and Boggs Mountain Demonstration State Forest on your list if you want to see more of the area.
How can I get to and around Middletown?
You can map out your trip in and around Middletown ahead of time with these transportation options. Fly into Santa Rosa, CA (STS-Sonoma County), which is located 19.6 mi (31.6 km) from the heart of the city. If you’d like to explore around the area, you may want a rental car for your journey.