A mountainous landscape with autumn foliage, rocky outcrops, and a valley below.

Villas in Middletown

  • 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

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21
No exact matches found, but these alternatives could be just right

Recommended hotels in Middletown

A large brick building with a central entrance, multiple windows, and a covered walkway.

1. Wayside Inn

Wayside Inn
3.5 star property
Middletown
9.2 out of 10, Wonderful, (459 reviews)
"We very much enjoyed our night at the Inn. Historic, charming, unique. The people we met were attentive and friendly. Our room was clean and quiet throughout the night. The onsite restaurant served delicious food both at dinner and breakfast."
United States
Susan
$88 nightly
The price is $97
Nov 29 - Nov 30
Total with taxes and fees
Wayside Inn
A hotel entrance with a covered walkway, a parking lot, and a building with a grey roof.

2. Econo Lodge Inn & Suites Middletown - Winchester South

Econo Lodge Inn & Suites Middletown - Winchester South
2.0 star property
Middletown
5.8 out of 10, (332 reviews)
"Place is in poor repair."
United States
Craig
$65 nightly
The price is $71
Nov 22 - Nov 23
Total with taxes and fees
Econo Lodge Inn & Suites Middletown - Winchester South
A hotel with a green roof, a covered entrance, and a sign that reads "RAMADA".

3. Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley
2.5 star property
Strasburg
8.2 out of 10, Very good, (1,017 reviews)
"A really great hotel for the price"
United States
Glenn
$76 nightly
The price is $84
Nov 8 - Nov 9
Total with taxes and fees
Ramada by Wyndham Strasburg/Shenandoah Valley
A rectangular swimming pool with a brick wall and trees in the background.

4. Holiday Inn Express Winchester South-Stephens City by IHG

Holiday Inn Express Winchester South-Stephens City by IHG
2.5 star property
Stephens City
8.2 out of 10, Very good, (919 reviews)
"Great hotel"
United States
Michael
$83 nightly
The price is $92
Nov 29 - Nov 30
Total with taxes and fees
Holiday Inn Express Winchester South-Stephens City by IHG
A multi-story hotel with a prominent sign for Marriott.

5. Fairfield Inn & Suites Strasburg Shenandoah Valley

Fairfield Inn & Suites Strasburg Shenandoah Valley
3.0 star property
Strasburg
9.0 out of 10, Wonderful, (1,001 reviews)
"Very clean room and property. Staff was great. Breakfast was good."
United States
Kayla
$127 nightly
The price is $142
Nov 8 - Nov 9
Total with taxes and fees
Fairfield Inn & Suites Strasburg Shenandoah Valley
A two-story building with a brick facade and a beige exterior.

6. Quality Inn Stephens City - Winchester South

Quality Inn Stephens City - Winchester South
2.5 star property
Stephens City
8.0 out of 10, Very good, (722 reviews)
"Rooms were clean and comfortable"
United States
Jeanne
$78 nightly
The price is $87
Nov 30 - Dec 1
Total with taxes and fees
Quality Inn Stephens City - Winchester South
A Comfort Inn & Suites building with a modern design, featuring a prominent logo on the facade, a covered entrance, and multiple windows.

7. Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
2.5 star property
Winchester
9.6 out of 10, Exceptional, (1,143 reviews)
"Nice hotel. I would stay here again."
United States
Kenneth
$100 nightly
The price is $111
Nov 22 - Nov 23
Total with taxes and fees
Comfort Inn & Suites Winchester
A Country Inn & Suites by Radisson building with a covered entrance and multiple windows.

8. Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA
3.0 star property
Winchester
8.8 out of 10, Excellent, (1,006 reviews)
"Comfortable bed, friendly staff, and convenient location"
United States
Zohair
$85 nightly
The price is $95
Nov 29 - Nov 30
Total with taxes and fees
Country Inn & Suites by Radisson, Winchester, VA
A Hampton Inn with a covered entrance and a parking lot.

9. Hampton Inn Front Royal

Hampton Inn Front Royal
2.5 star property
Front Royal
9.2 out of 10, Wonderful, (1,000 reviews)
"The hotel was really well maintained inside and out! Room was super-clean."
United States
Tammy
$111 nightly
The price is $124
Nov 29 - Nov 30
Total with taxes and fees
Hampton Inn Front Royal
A brick building with a sign reading "HOULIHAN'S RESTAURANT + BAR".

10. DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows
4.0 star property
Front Royal
9.0 out of 10, Wonderful, (1,003 reviews)
"Clean Hotel, nice decor, and lovely hot tub after hiking!"
United States
rebecca
$127 nightly
The price is $140
Nov 23 - Nov 24
Total with taxes and fees
DoubleTree by Hilton Front Royal Blue Ridge Shadows
A multi-story hotel with a swimming pool, parking lot, and a landscaped area.

11. TownePlace Suites by Marriott Front Royal

TownePlace Suites by Marriott Front Royal
3.0 star property
Front Royal
9.6 out of 10, Exceptional, (615 reviews)
"Cleaned, maintained hotel near many conveniences."
United States
JoEllen
$137 nightly
The price is $151
Nov 29 - Nov 30
Total with taxes and fees
TownePlace Suites by Marriott Front Royal
A hotel with a modern design, featuring a prominent 'spark by Hilton' sign, a well-lit entrance, and a landscaped front yard.

12. Spark by Hilton Winchester

Spark by Hilton Winchester
3.0 star property
Winchester
9.2 out of 10, Wonderful, (1,005 reviews)
"Clean room, great staff, good parking and free breakfast"
United States
Albert
$65 nightly
The price is $74
Nov 15 - Nov 16
Total with taxes and fees
Spark by Hilton Winchester
A brick building with a sign reading "Motel" and a neon sign for "Relax Inn" on the right.

13. Relax Inn Motel

Relax Inn Motel
2.0 star property
Front Royal
8.4 out of 10, Very good, (304 reviews)
"It is very close to the national park north entrance."
United States
xiangqing
$65 nightly
The price is $72
Nov 29 - Nov 30
Total with taxes and fees
Relax Inn Motel
A Super 8 hotel with a brick facade, multiple windows, and a central entrance.

14. Super 8 by Wyndham Front Royal Near Shenandoah National Park

Super 8 by Wyndham Front Royal Near Shenandoah National Park
2.0 star property
Front Royal
7.6 out of 10, Good, (1,000 reviews)
"Great location and comfortable room."
United States
Amelia
$72 nightly
The price is $76
Nov 16 - Nov 17
Total with taxes and fees
Super 8 by Wyndham Front Royal Near Shenandoah National Park
A row of white buildings with blue shutters, a covered walkway, and a white fence.

15. Motel 6 Front Royal, VA

Motel 6 Front Royal, VA
2.0 star property
Front Royal
7.0 out of 10, Good, (571 reviews)
"Property was clean staff was very nice polite and helpful They looked like they are doing some upgrades which is always nice to see I will be staying here again"
United States
Matthew
$58 nightly
The price is $65
Nov 4 - Nov 5
Total with taxes and fees
Motel 6 Front Royal, VA
A multi-story hotel with a courtyard, outdoor seating, and a guest parking area.

16. Baymont by Wyndham Front Royal Near Shenandoah National Park

Baymont by Wyndham Front Royal Near Shenandoah National Park
2.5 star property
Front Royal
6.4 out of 10, (1,002 reviews)
"Great breakfast nice room"
Netherlands
pieter
$60 nightly
The price is $66
Dec 1 - Dec 2
Total with taxes and fees
Baymont by Wyndham Front Royal Near Shenandoah National Park
An outdoor patio with a grill, seating, and string lights.

17. Home2 Suites By Hilton Winchester

Home2 Suites By Hilton Winchester
3.0 star property
Winchester
9.4 out of 10, Exceptional, (43 reviews)
"Clean rooms , friendly staff."
United States
Jean
$88 nightly
The price is $100
Nov 22 - Nov 23
Total with taxes and fees
Home2 Suites By Hilton Winchester
A motel with a swimming pool, a speed limit sign, and a parking lot.

18. Twi-Lite Inn

Twi-Lite Inn
2.0 star property
Front Royal
8.2 out of 10, Very good, (589 reviews)
"Very clean and comfortable room!"
United States
Victoria
$82 nightly
The price is $91
Dec 1 - Dec 2
Total with taxes and fees
Twi-Lite Inn
A Fairfield by Marriott hotel with a modern entrance, stone pillars, and a well-lit facade.

19. Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
3.0 star property
Winchester
9.2 out of 10, Wonderful, (964 reviews)
"Great place to stay in Winchester."
United States
Thomas
$93 nightly
The price is $103
Nov 8 - Nov 9
Total with taxes and fees
Fairfield Inn & Suites by Marriott Winchester
A hotel entrance with a covered waiting area, brick facade, and a clear sky.

20. Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester
2.5 star property
Winchester
8.6 out of 10, Excellent, (1,091 reviews)
"Nice clean stay!"
United States
Pamela
$70 nightly
The price is $77
Dec 1 - Dec 2
Total with taxes and fees
Travelodge by Wyndham Winchester
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 Middletown Hotel Reviews

TRU By Hilton Winchester

TRU By Hilton Winchester

10/10 Excellent
"This a very nice place to stay. The breakfast hit the spot. We would stay here again."
Betsy 1-night trip
Posted 3 hours ago
TRU By Hilton Winchester

Find out more about Middletown

Middletown Villas information

Number of reviews
7,240
Accommodation
6 Villas
Lowest Price
$65
Highest Price
$151

Frequently asked questions

Why book your villa in Middletown with Expedia?
Reserving a villa in Middletown is as simple as entering your travel dates and choosing an option that checks your boxes. Seeking something luxurious or low cost, or a stay that also has a pool and free WiFi? Use Expedia's search filters to narrow your results and find your perfect match.
How can I find cheap villas in Middletown?
With Expedia's useful filter tool, reserving cheap villas in Middletown has never been easier. To discover stays that'll make your wallet happy, narrow your search results by star rating, budget and amenities.
What is there to do near my villa in Middletown?
The best travel accessory is a well-planned itinerary. Belle Grove Plantation is a wonderful spot to kick off your exploration of Middletown.

Explore a world of travel with Expedia