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Check prices for these dates

Next weekend
6 Jun - 8 Jun
In two weeks
13 Jun - 15 Jun
In one month
27 Jun - 29 Jun
In two months
25 Jul - 27 Jul

Compare 115 Cottages in Middletown with updated reviews, rates, and availability.

Private Wine County Retreat in Calistoga, walk to downtown!
Terrace/patio

Private Wine County Retreat in Calistoga, walk to downtown!

9.8 out of 10, Exceptional, (17)
"We have stayed many times at the Cottage Grove Inn and it never disappoints. "
The price is AED 1,098
AED 1,499 total
includes taxes & fees
2 Jun - 3 Jun
Private Wine County Retreat in Calistoga, walk to downtown!
Wine Country Bungalow
Fridge, microwave, oven, stovetop

Wine Country Bungalow

9.8 out of 10, Exceptional, (44)
"Pleasant neighborhood for a family stay."
Wine Country Bungalow
Hidden Wine Country Cottage in Downtown Calistoga
Terrace/patio

Hidden Wine Country Cottage in Downtown Calistoga

10.0 out of 10, Exceptional, (1)
"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 AED 1,098
AED 1,499 total
includes taxes & fees
2 Jun - 3 Jun
Hidden Wine Country Cottage in Downtown Calistoga
Comfort and Style in Our Queen Cottage
Dining

Comfort and Style in Our Queen Cottage

9.8 out of 10, Exceptional, (47)
"Wonderful time in Calistoga "
The price is AED 694
AED 929 total
includes taxes & fees
1 Jun - 2 Jun
Comfort and Style in Our Queen Cottage
Backyard Garden Oasis
Deep-tissue massages, Swedish massages, prenatal massages, massages

Backyard Garden Oasis

3.0 star property
9.6 out of 10, Exceptional, (45)
"perfect place"
The price is AED 713
AED 795 total
includes taxes & fees
30 May - 31 May
Backyard Garden Oasis
Chalk Hill Cottage Close to Wineries
Exterior

Chalk Hill Cottage Close to Wineries

9.8 out of 10, Exceptional, (36)
"The cottage was spacious and in a great location."
Chalk Hill Cottage Close to Wineries
Sunny View Cottage in the Beautiful Wine Country
Fridge, microwave, oven, stovetop

Sunny View Cottage in the Beautiful Wine Country

10.0 out of 10, Exceptional, (267)
"Wonderful cottage with all the amenities in a great location to explore all the area has to offer."
Sunny View Cottage in the Beautiful Wine Country
Dry Creek Cottage - Healdsburg
Pool

Dry Creek Cottage - Healdsburg

9.8 out of 10, Exceptional, (148)
"We had a great stay!"
Dry Creek Cottage - Healdsburg
1 Bedroom Cottage Walking Distance to Down Town
Fridge, microwave, oven, stovetop

1 Bedroom Cottage Walking Distance to Down Town

10.0 out of 10, Exceptional, (53)
"I had a great stay at this cozy VRBO cottage while attending a K9 training program. The home was clean, comfortable, and just a short 1.5-block walk to a lovely neighborhood park—perfect for unwinding after training sessions. The backyard was a great bonus, with a picnic table to relax and enjoy the fresh air. Highly recommend for anyone looking for a quiet, convenient stay!"
1 Bedroom Cottage Walking Distance to Down Town
TREE HOUSE, WITH INDOOR/OUTDOOR SHOWER, PRIVATE DECK, POOL & INFIINITY HOT TUB
Exterior

TREE HOUSE, WITH INDOOR/OUTDOOR SHOWER, PRIVATE DECK, POOL & INFIINITY HOT TUB

TREE HOUSE, WITH INDOOR/OUTDOOR SHOWER, PRIVATE DECK, POOL & INFIINITY HOT TUB
Waterfront Cottage w/ Private Pool & Lake View!
Fridge, microwave, stovetop, dishwasher

Waterfront Cottage w/ Private Pool & Lake View!

9.2 out of 10, Wonderful, (40)
"Nice little house, good for a couple or small family. Great view of the lake in the back yard."
Waterfront Cottage w/ Private Pool & Lake View!
Mem Day Special! 20% off motor water sports rentals & 100 off non motor rentals!
Miscellaneous

Mem Day Special! 20% off motor water sports rentals & 100 off non motor rentals!

9.4 out of 10, Exceptional, (15)
"We had such a good time. The lake was close by so we got to enjoy all our toys. Angelique was super nice very relaxed environment. Pet friendly and our dogs had a great time."
Mem Day Special! 20% off motor water sports rentals & 100 off non motor rentals!
Heron House--The River House in the Redwoods
Outdoor spa tub

Heron House--The River House in the Redwoods

10.0 out of 10, Exceptional, (23)
"Home is situated in a very quiet and scenic location on the river, with a nice deck with outside dining and hot tub. Property had kayaks and other river equipment available, too. Home was clean, with a lovely kitchen and rooms. We would stay here again. "
Heron House--The River House in the Redwoods
Great Price! Sunset Beach Cottage with Lovely garden, beach, and boat dock!
Miscellaneous

Great Price! Sunset Beach Cottage with Lovely garden, beach, and boat dock!

9.8 out of 10, Exceptional, (28)
"Beautiful property in a beautiful location. "
Great Price! Sunset Beach Cottage with Lovely garden, beach, and boat dock!
Russian Riverside Cottage in Healdsburg
Living area

Russian Riverside Cottage in Healdsburg

8.6 out of 10, Excellent, (9)
"We really enjoyed our stay. The communication with owner was great and we will come back again. The beach is just right there and our young adult grandchildren love it."
Russian Riverside Cottage in Healdsburg
Mountain Cottage near Russian River, hiking & downtown, family and pet friendly
Terrace/patio

Mountain Cottage near Russian River, hiking & downtown, family and pet friendly

9.2 out of 10, Wonderful, (55)
"Cute property! It’s a little rustic, but has everything you need. The location is beautiful and convenient to Healdsburg. "
Mountain Cottage near Russian River, hiking & downtown, family and pet friendly
Healdsburg Cottage Walk to the Plaza, Workspace
Terrace/patio

Healdsburg Cottage Walk to the Plaza, Workspace

10.0 out of 10, Exceptional, (226)
"This is a wonderful place to stay - very homey, clean, comfortable and beautiful with everything we needed. I hope to be able to stay there again sometime. "
Healdsburg Cottage Walk to the Plaza, Workspace
Vineyard View Home with a Complimentary Wine Tasting
Dining

Vineyard View Home with a Complimentary Wine Tasting

9.0 out of 10, Wonderful, (6)
"My mom and I loved our stay in Calistoga. Brittany was a great host, and even went out of her way to find us a driver on the days we went tasting at vineyards. We would definitely stay here again!"
Vineyard View Home with a Complimentary Wine Tasting
Private 1-bedroom Guest House with Great Amenities
Terrace/patio

Private 1-bedroom Guest House with Great Amenities

10.0 out of 10, Exceptional, (11)
"Our group had a wonderful time. The property was perfect in every way & would certainly rent again if lucky enough to return to Healdsburg."
Private 1-bedroom Guest House with Great Amenities
Warm And Cozy Mountain And Lake View Haven 2 Bedroom Cottage by RedAwning
Cottage, 2 Bedrooms | Private kitchen | Fridge, oven, coffee/tea maker, toaster

Warm And Cozy Mountain And Lake View Haven 2 Bedroom Cottage by RedAwning

3.0 star property
The price is AED 682
AED 1,774 total
includes taxes & fees
25 Jun - 26 Jun
Warm And Cozy Mountain And Lake View Haven 2 Bedroom Cottage by RedAwning
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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Frequently asked questions

How much do cottages in Middletown cost?
Prepare to pay between AED 682 and AED 1,098 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.
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.