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Check prices for these dates

In two weeks
22 May - 24 May
In two months
3 Jul - 5 Jul
In three months
31 Jul - 2 Aug
In four months
28 Aug - 30 Aug

Our top choices for Middletown cottages

Exterior

Backyard Garden Oasis

Backyard Garden Oasis
3.0 star property
Middletown
9.6 out of 10, Exceptional, (51 reviews)
"Cute garden area, quiet, nice all inclusive spot"
United States
Jodi
The price is €199
includes taxes & fees
9 May - 10 May
Backyard Garden Oasis
Outdoor dining

Garden house with gas fireplace

Garden house with gas fireplace
Middletown
10.0 out of 10, Exceptional, (1 review)
"We were not originally planning on staying in Middletown but were pleasantly surprised on arrival. The Garden House is very comfortable and convenient to many things in town. Linda, our host had special little touches that made the stay relaxing. Number one the shower is amazing! I looked forward to it every evening the pressure and hot water is perfect and the quality shampoos and soaps provides smelled wonderful! The kitchen is well stocked if you are cooking during your stay. And there is...
United States
kelsie i.
The price is €209
includes taxes & fees
17 May - 18 May
Garden house with gas fireplace
Exterior

Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed

Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed
Calistoga
10.0 out of 10, Exceptional, (3 reviews)
"Yes, our little buddy was welcome!"
United States
Doug G.
The price is €327
includes taxes & fees
13 May - 14 May
Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed
Smart TV, fireplace

Wine Country Cottage in downtown Santa Rosa, CA

Wine Country Cottage in downtown Santa Rosa, CA
Santa Rosa
9.6 out of 10, Exceptional, (73 reviews)
"We stayed for a girls weekend for a napa get away. and we brought the dog and it was a great stay. And clean too. Easy for a home base. And it was affordable. Would stay again "
United States
Valerie C.
The price is €351
includes taxes & fees
12 May - 13 May
Wine Country Cottage in downtown Santa Rosa, CA
Exterior

Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown

Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown
Calistoga
9.8 out of 10, Exceptional, (39 reviews)
"Perfect little cottage within walking distance to everything in downtown Calistoga! Bed was so comfy and the fireplace made it feel extra cozy. We definitely want to stay here again!"
United States
Cameron D.
The price is €338
includes taxes & fees
11 May - 12 May
Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown
House (2 Bedrooms) | Interior

Watefront Getaway w/ Mtn Views & Dock in Clearlake

Watefront Getaway w/ Mtn Views & Dock in Clearlake
3.0 star property
Clearlake
The price is €230
includes taxes & fees
10 May - 11 May
Watefront Getaway w/ Mtn Views & Dock in Clearlake
Terrace/patio

Escape to wine country in your independent cottage in downtown Calistoga

Escape to wine country in your independent cottage in downtown Calistoga
Calistoga
10.0 out of 10, Exceptional, (3 reviews)
"We made the Calistoga CA area our base for our recent trip and the Cottage Grove Inn served as a great place to stay."
United States
Anonymous traveller
The price is €315
includes taxes & fees
11 May - 12 May
Escape to wine country in your independent cottage in downtown Calistoga
Exterior

Charming King Cottage

Charming King Cottage
Calistoga
9.8 out of 10, Exceptional, (11 reviews)
"Nice comfortable cottage."
United States
Michael E. S.
The price is €232
includes taxes & fees
13 May - 14 May
Charming King Cottage
Dining

Comfort and Style in Our Queen Cottage

Comfort and Style in Our Queen Cottage
Calistoga
9.8 out of 10, Exceptional, (49 reviews)
"Great place to stay. Clean and well appointed and in a great location for access to sites, vineyards, and restaurants "
United States
Robert
The price is €200
includes taxes & fees
13 May - 14 May
Comfort and Style in Our Queen Cottage
Outdoor spa tub

The Carriage House Sonoma • Hot Tub • Vineyard Views • Complimentary Bottle

The Carriage House Sonoma • Hot Tub • Vineyard Views • Complimentary Bottle
Kenwood
9.0 out of 10, Wonderful, (2 reviews)
"Such a cute place! The turn into the property is a bit hidden right before the bridge but once you find it the house is so secluded with plenty of space. The kitchen was fully stocked and had everything you could think of. Did a wine tasting with their tasting room and everyone was so welcoming and sweet. Thank you! "
United States
Sara W.
The price is €527
includes taxes & fees
11 May - 12 May
The Carriage House Sonoma • Hot Tub • Vineyard Views • Complimentary Bottle
1 bedroom, iron/ironing board, Internet, bed sheets

RustRidge Bed and Breakfast - Rustridge Cottage

RustRidge Bed and Breakfast - Rustridge Cottage
St Helena
8.0 out of 10, Very good, (3 reviews)
"We had a magical time. The horses, pool, Vinyard and hospitality was wonderful. What a special ranch. Oh and the breakfast! Delicious!!"
United States
ila m.
The price is €488
includes taxes & fees
7 Jun - 8 Jun
RustRidge Bed and Breakfast - Rustridge Cottage
Exterior detail

Farm Country Cottage in Downtown Geyserville, Vineyard Views + UNTI Wine

Farm Country Cottage in Downtown Geyserville, Vineyard Views + UNTI Wine
Geyserville
10.0 out of 10, Exceptional, (2 reviews)
"Cozy, rustic, and with all great amenities."
United States
Gina I.
The price is €311
includes taxes & fees
19 May - 20 May
Farm Country Cottage in Downtown Geyserville, Vineyard Views + UNTI Wine
Microwave, oven, stovetop, dishwasher

Enchanting Vineyard cottage nestled in the wine country!

Enchanting Vineyard cottage nestled in the wine country!
Santa Rosa
The price is €600
includes taxes & fees
11 May - 12 May
Enchanting Vineyard cottage nestled in the wine country!
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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Top Middletown Hotel Reviews

Hotel E

Hotel E

10/10 Excellent
"I love Hotel E. I booked rooms twice within one week, and not only is the space lovely, but so are the employees. Chris L. at the front desk went out of his way to help me keep my gear safe, and I felt like I could trust him and the hotel. I’ll definitely be booking here every time I’m in town. Thank you also to Ingrid for being so helpful and friendly. The rooms were clean and comfortable. Thanks, Hotel E!"
alana 1-night trip
Posted 1 hour ago
Hotel E

Find out more about Middletown

Middletown Cottages information

Number of reviews
113
Accommodation
123 Cottages
Lowest Price
€199
Highest Price
€600

Frequently asked questions

How much do cottages in Middletown cost?
Prepare to pay between €199 and €600 per night for cottages in Middletown. No matter your budget, a wonderful stay is just a click or two away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Are there any family-friendly cottages in Middletown?
If you're looking to get back to nature in Middletown, we recommend Backyard Garden Oasis. With a 3-star rating and amenities like pillow top mattresses and a barbecue grill, you'll find it easy to settle in at this family-friendly cottage. Check in to your hotel and then make your way to some attractions that will keep everyone entertained in Middletown. Cobb Mountain should be at the top of your list.
Why book your cottage in Middletown with Expedia?
We think a getaway should be a walk in the park, so if you're looking for cottages in Middletown at an affordable rate, Expedia has your back. Save those pennies and choose an economical option far from the hustle and bustle, or splurge on a 5-star cottage to treat your loved ones.
How can I find cheap cottages in Middletown?
With Expedia's user-friendly filter tool, sourcing cheap cottages in Middletown is a breeze. To discover properties that are friendly on the wallet, narrow your search results by amenities, star rating and budget.
What is there to do in Middletown near my cottage?
Once you've checked in to your hotel, set out and discover the awesome things Middletown has on offer. Beaver Creek Vineyards is a top attraction to add to your must-see list.