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Check prices for these dates

In two weeks
17 Oct - 19 Oct
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec
In four months
23 Jan - 25 Jan

Featured Cottages in Middletown and around

Backyard Garden Oasis
Exterior

Backyard Garden Oasis

3.0 star property
9.6 out of 10, Exceptional, (51)
"Cute garden area, quiet, nice all inclusive spot"
The price is €184
includes taxes & fees
6 Oct - 7 Oct
Backyard Garden Oasis
Garden house with gas fireplace
Outdoor dining

Garden house with gas fireplace

10.0 out of 10, Exceptional, (1)
"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...
The price is €204
includes taxes & fees
4 Nov - 5 Nov
Garden house with gas fireplace
Wine Country Cottage in downtown Santa Rosa, CA
Exterior

Wine Country Cottage in downtown Santa Rosa, CA

9.8 out of 10, Exceptional, (58)
"brilliant place to stay in central Santa Rosa downtown. Awesome access to downtown. Everything within walking distance. Thanks for a great stay"
The price is €347
includes taxes & fees
7 Oct - 8 Oct
Wine Country Cottage in downtown Santa Rosa, CA
Escape to Wine Country in your independant Cottage in Downtown Calistoga
Exterior

Escape to Wine Country in your independant Cottage in Downtown Calistoga

10.0 out of 10, Exceptional, (2)
"Loved everything Ellen was very accommodating ,pleasant and polite As well as professional The furnishings were very up scale and same style as my home One suggestion The tv should be more accessible so it does not block AC when pulled out from the wall I’m not being critical because I love this place. I will stay there every time I would ever be close to Calistoga. AND I adore Ellen personally and professionally!!👍❤️"
The price is €358
includes taxes & fees
2 Nov - 3 Nov
Escape to Wine Country in your independant Cottage in Downtown Calistoga
Windmill Cottage - Peaceful & Quiet on 5 acres
Property grounds

Windmill Cottage - Peaceful & Quiet on 5 acres

10.0 out of 10, Exceptional, (12)
"Joshua was the best host! "
The price is €411
includes taxes & fees
6 Oct - 7 Oct
Windmill Cottage - Peaceful & Quiet on 5 acres
True Wine Country Living: 2BR Converted Milkbarn on Family Vineyard
Property grounds

True Wine Country Living: 2BR Converted Milkbarn on Family Vineyard

10.0 out of 10, Exceptional, (11)
"Ideal for a relaxing time in wine country! The winery on property is fantastic and highly recommend it!"
The price is €507
includes taxes & fees
6 Oct - 7 Oct
True Wine Country Living: 2BR Converted Milkbarn on Family Vineyard
Escape to Wine County in your independant Cottage in Downtown Calistoga
Exterior

Escape to Wine County in your independant Cottage in Downtown Calistoga

9.6 out of 10, Exceptional, (26)
"Great cottage near downtown. "
The price is €356
includes taxes & fees
2 Nov - 3 Nov
Escape to Wine County in your independant Cottage in Downtown Calistoga
Escape to wine country in your independent cottage in downtown Calistoga
Terrace/patio

Escape to wine country in your independent cottage in downtown Calistoga

10.0 out of 10, Exceptional, (3)
"We made the Calistoga CA area our base for our recent trip and the Cottage Grove Inn served as a great place to stay."
The price is €351
includes taxes & fees
4 Nov - 5 Nov
Escape to wine country in your independent cottage in downtown Calistoga
Charming King Cottage
Property grounds

Charming King Cottage

9.8 out of 10, Exceptional, (11)
"Cozy and great price!"
The price is €434
includes taxes & fees
2 Nov - 3 Nov
Charming King Cottage
Comfort and Style in Our Queen Cottage
Property grounds

Comfort and Style in Our Queen Cottage

9.8 out of 10, Exceptional, (49)
"Great place to stay. Clean and well appointed and in a great location for access to sites, vineyards, and restaurants "
The price is €411
includes taxes & fees
2 Nov - 3 Nov
Comfort and Style in Our Queen Cottage
Vineyard Cottage • Hot Tub • Bottle of Wine & Wine Tasting Included
Outdoor spa tub

Vineyard Cottage • Hot Tub • Bottle of Wine & Wine Tasting Included

4.5 star property
9.0 out of 10, Wonderful, (2)
"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! "
The price is €440
includes taxes & fees
4 Nov - 5 Nov
Vineyard Cottage • Hot Tub • Bottle of Wine & Wine Tasting Included
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

Holiday Inn Windsor Wine Country by IHG

Holiday Inn Windsor Wine Country by IHG

10/10 Excellent
"Staff is very helpful and overall stay was great. "
Carmen 2-night trip
Posted 1 day ago
Holiday Inn Windsor Wine Country by IHG

Find out more about Middletown

Find out more about Middletown

Middletown Cottages information

Number of reviews
200
Accommodation
117 Cottages
Lowest Price
€184
Highest Price
€507

Frequently asked questions

How much do cottages in Middletown cost?
Prepare to pay between €184 and €507 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia