Photo by Brittany Davidson

Search Middlebrook Cottages

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

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Jan 2 - Jan 4
In two weeks
Jan 9 - Jan 11
In one month
Jan 23 - Jan 25
In two months
Feb 20 - Feb 22

Our top choices for Middlebrook cottages

Terrace/patio
Bluebird Cottage: Near 151 + Appalachian Trail

Cottage in Roseland

Bluebird Cottage: Near 151 + Appalachian Trail
2.0 star property
8.4 out of 10, Very Good, (9)
"I contacted the owners to see if my family and I could check in earlier and they were about to accommodate for us. The home was clean, spacious, and had everything we needed for our stay."
United States
Sa'Mone M.
$275 nightly
The price is $292
Jan 5 - Jan 6, 2026
Total with taxes and fees
Bluebird Cottage: Near 151 + Appalachian Trail
Exterior
The Woodland Cottage charming 2 bedoom one bath with deck on back, covered front

Cottage in Buena Vista

The Woodland Cottage charming 2 bedoom one bath with deck on back, covered front
9.6 out of 10, Exceptional, (15)
"Very nice and clean property in a quiet neighborhood. Host communicated well and left many amenities for us. Loved our stay!"
United States
Tina F.
$172 nightly
The price is $191
Dec 30 - Dec 31
Total with taxes and fees
The Woodland Cottage charming 2 bedoom one bath with deck on back, covered front
Property grounds
The Cottage at Batten Green, Beautiful Farm Views, 5 mins to DT Staunton, Pet-Friendly!

Cottage in Staunton

The Cottage at Batten Green, Beautiful Farm Views, 5 mins to DT Staunton, Pet-Friendly!
10.0 out of 10, Exceptional, (1)
"Beautiful grounds and views. Pet friendly in some suites the cottage"
United States
Carina
$225 nightly
The price is $245
Jan 12 - Jan 13, 2026
Total with taxes and fees
The Cottage at Batten Green, Beautiful Farm Views, 5 mins to DT Staunton, Pet-Friendly!
Exterior
Deerfield Honeymoon Cottage at Autumn Ridge

Cottage in Lexington

Deerfield Honeymoon Cottage at Autumn Ridge
9.8 out of 10, Exceptional, (40)
"this was such a terrific stay! very well ran and amazing hosts! "
United States
Darcy T.
$318 nightly
The price is $367
Dec 23 - Dec 24
Total with taxes and fees
Deerfield Honeymoon Cottage at Autumn Ridge
Outdoor dining
Rustic Romantic Bayberry Cottage at Autumn Ridge

Cottage in Lexington

Rustic Romantic Bayberry Cottage at Autumn Ridge
9.8 out of 10, Exceptional, (31)
"Had a great stay!"
United States
Erin C.
$277 nightly
The price is $320
Dec 30 - Dec 31
Total with taxes and fees
Rustic Romantic Bayberry Cottage at Autumn Ridge
Exterior
Twinleaf Honeymoon Cottage at Autumn Ridge

Cottage in Lexington

Twinleaf Honeymoon Cottage at Autumn Ridge
9.8 out of 10, Exceptional, (13)
"Great location. Very quiet and clean. A great stay!!!"
United States
Erik T.
$301 nightly
The price is $346
Dec 23 - Dec 24
Total with taxes and fees
Twinleaf Honeymoon Cottage at Autumn Ridge
Exterior
Autumn Ridge Cottages

Cottage in Lexington

Autumn Ridge Cottages
2.5 star property
9.0 out of 10, Wonderful, (180)
"Very nicely appointed, clean, quiet, quaint, and close to family. "
United States
Gary
$375 nightly
The price is $432
Jan 7 - Jan 8, 2026
Total with taxes and fees
Autumn Ridge Cottages
Exterior
The Knox Cottage - Luxury Farm Stay

Cottage in Lexington

The Knox Cottage - Luxury Farm Stay
10.0 out of 10, Exceptional, (1)
"It was wonderful!"
United States
Patricia C.
$365 nightly
The price is $406
Dec 23 - Dec 24
Total with taxes and fees
The Knox Cottage - Luxury Farm Stay
Exterior
3 BR house with hot tub near Lexington and surrounding attractions!

Vacation Home in Glasgow

3 BR house with hot tub near Lexington and surrounding attractions!
9.8 out of 10, Exceptional, (54)
"Beautiful property with amazing amenities available for use. The host, Tasha, went above and beyond to make sure that we were comfortable and it felt like home. An absolutely wonderful experience!"
United States
Julia P.
$234 nightly
The price is $270
Dec 23 - Dec 24
Total with taxes and fees
3 BR house with hot tub near Lexington and surrounding attractions!
Property grounds
Rustic Romantic Ridgeview Cottage at Autumn Ridge

Cottage in Lexington

Rustic Romantic Ridgeview Cottage at Autumn Ridge
8.0 out of 10, Very Good, (2)
"Lovely cabin with an amazing view of the Blue Ridge!"
United States
Cindy A.
$368 nightly
The price is $424
Dec 28 - Dec 29
Total with taxes and fees
Rustic Romantic Ridgeview Cottage at Autumn Ridge
Exterior
The Monroe Cottage - Luxury Farm Stay

Cottage in Lexington

The Monroe Cottage - Luxury Farm Stay
$365 nightly
The price is $406
Dec 23 - Dec 24
Total with taxes and fees
The Monroe Cottage - Luxury Farm Stay
Exterior
The Scout Cottage - Luxury Farm Stay

Cottage in Lexington

The Scout Cottage - Luxury Farm Stay
$365 nightly
The price is $406
Dec 23 - Dec 24
Total with taxes and fees
The Scout Cottage - Luxury Farm Stay
Exterior
The Sunday Cottage - Luxury Farm Stay

Cottage in Lexington

The Sunday Cottage - Luxury Farm Stay
$370 nightly
The price is $411
Dec 23 - Dec 24
Total with taxes and fees
The Sunday Cottage - Luxury Farm Stay
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 Middlebrook Hotel Reviews

Holiday Inn Express & Suites Staunton by IHG

Holiday Inn Express & Suites Staunton by IHG

10/10 Excellent
"Tim at the front desk was so accommodating and helpful! We saw him when we got in late at night and when we checked out the next morning. Thank you Tim!"
Samuel 1-night trip
Posted 1 day ago
Holiday Inn Express & Suites Staunton by IHG

Find out more about Middlebrook

Middlebrook Cottages information

Number of reviews
172
Accommodation
77 Cottages
Lowest Price
$191
Highest Price
$432

Frequently asked questions

Why book your cottage in Middlebrook with Expedia?
Expedia has some excellent cottages in Middlebrook, so start packing your bags for a memorable vacation close to nature. If you have a certain budget, choose how much you're willing to spend and the preferred star rating of your property. Or, use our filters to search for cottages with a hot tub or free WiFi. We'll help you find the right fit whatever your escape looks like.
How can I find cheap cottages in Middlebrook?
An excellent way to get cheap cottages in Middlebrook is with Expedia's handy filter tool. Fine-tune your search results by star rating, budget and amenities to access excellent rates in just a few clicks.

Explore a world of travel with Expedia