Photo by Stephanie Sutton

Search Vacation Homes in Middletown

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

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

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

Vacation Homes in Middletown

Lone Bear Cabin: Lv2 EV, WiFi, River Access, Mountain Views, fireplace, hot tub
Pool

Lone Bear Cabin: Lv2 EV, WiFi, River Access, Mountain Views, fireplace, hot tub

10.0 out of 10, Exceptional, (98)
"Clean and nice place to stay to visit Shenandoah "
The price is AED 624
AED 1,503 total
includes taxes & fees
7 Oct - 8 Oct
Lone Bear Cabin: Lv2 EV, WiFi, River Access, Mountain Views, fireplace, hot tub
Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly
Property grounds

Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly

9.6 out of 10, Exceptional, (196)
"We loved everything about our stay. The views were spectacular and the setting was so tranquil. "
Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly
Gorgeous getaway: 10 private acres w/ Hot Tub in GW forest near Shenandoah River
Dining

Gorgeous getaway: 10 private acres w/ Hot Tub in GW forest near Shenandoah River

9.8 out of 10, Exceptional, (32)
"The Chateau was fabulous! As described, private, zen-like, very comfortable with a great deck, views and large outback hot tub. "
Gorgeous getaway: 10 private acres w/ Hot Tub in GW forest near Shenandoah River
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Outdoor dining

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails

9.8 out of 10, Exceptional, (234)
"Wonderful location, beautiful as always. Looking forward to our next trip."
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Outdoor dining

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails

9.8 out of 10, Exceptional, (194)
"We love our time there. Cabin was amazing "
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Newly renovated Farm cottage with Mountain views
Outdoor dining

Newly renovated Farm cottage with Mountain views

10.0 out of 10, Exceptional, (36)
"The cottage is lovely, with modern kitchen and bath and charming furnishings throughout. Views are wonderful and the location is quiet, set well back from the road. The host is very prompt and courteous in communications. She went above and beyond the call of duty in helping us when I temporarily mislaid the key."
The price is AED 588
AED 1,191 total
includes taxes & fees
2 Oct - 3 Oct
Newly renovated Farm cottage with Mountain views
Secluded River Cabin Getaway (Masten Cabin)
Fridge, microwave, oven, stovetop

Secluded River Cabin Getaway (Masten Cabin)

9.8 out of 10, Exceptional, (163)
"A beautiful home and property. This is a wonderful weekend getaway home. Modern and comfortable, but especially quiet!"
Secluded River Cabin Getaway (Masten Cabin)
The Outpost: A Rustic Respite in the Shenandoah Valley 4 Bikes For Use Tesla Ch
Outdoor dining

The Outpost: A Rustic Respite in the Shenandoah Valley 4 Bikes For Use Tesla Ch

8.8 out of 10, Excellent, (42)
"Great environment, lots to do within the area. Check in process is very convenient. Every room feels like a new adventure."
The Outpost: A Rustic Respite in the Shenandoah Valley 4 Bikes For Use Tesla Ch
River Woods Retreat:10min to River, L2 EV, Hikes, 2 Fireplaces, Hottub, SP 10mi
Smart TV, fireplace, DVD player

River Woods Retreat:10min to River, L2 EV, Hikes, 2 Fireplaces, Hottub, SP 10mi

10.0 out of 10, Exceptional, (56)
"A beautiful cabin far from the hustle and bustle. Great place to relax. "
The price is AED 808
AED 1,552 total
includes taxes & fees
29 Oct - 30 Oct
River Woods Retreat:10min to River, L2 EV, Hikes, 2 Fireplaces, Hottub, SP 10mi
The Apple Mountain House
Dining

The Apple Mountain House

9.6 out of 10, Exceptional, (4)
"Amazing place to relax."
The price is AED 405
AED 1,326 total
includes taxes & fees
1 Oct - 2 Oct
The Apple Mountain House
Waterfront, Luxury Panoramic View, Fast Wi-Fi, Private River Access Steps Away!
Outdoor dining

Waterfront, Luxury Panoramic View, Fast Wi-Fi, Private River Access Steps Away!

10.0 out of 10, Exceptional, (53)
"Amaxing home beautifully decorated and just felt like home. Need a pmace just to relax and do nothing this is the place for you. Book your stay now i promise you wont be disappointed. Breathe taking river views and an awesome wrap around deck to enjoy that view "
Waterfront, Luxury Panoramic View, Fast Wi-Fi, Private River Access Steps Away!
Sunset Mountain Cabin
Terrace/patio

Sunset Mountain Cabin

9.8 out of 10, Exceptional, (35)
"We loved this little getaway spot! The view was gorgeous and the cabin was so clean and cozy!"
Sunset Mountain Cabin
Luxury Cabin Getaway in the Blue Ridge Mountains
Exterior

Luxury Cabin Getaway in the Blue Ridge Mountains

Luxury Cabin Getaway in the Blue Ridge Mountains
Cozy Lakeside Homestead
Outdoor dining

Cozy Lakeside Homestead

10.0 out of 10, Exceptional, (197)
"We had a wonderful time! The kids loved the games available and the hot tub. My husband absolutely loved the fire pit and we had a great time at the lake. Will definitely be coming back. "
The price is AED 771
AED 1,079 total
includes taxes & fees
6 Oct - 7 Oct
Cozy Lakeside Homestead
River Front Retreat
Dining

River Front Retreat

8.8 out of 10, Excellent, (43)
"We enjoyed our stay at this property. It was exactly what we were looking for for a peaceful weekend getaway."
River Front Retreat
Warm Welcoming Retreat in Shenandoah w/1 mile of River, Stunning Mountain View’s
Terrace/patio

Warm Welcoming Retreat in Shenandoah w/1 mile of River, Stunning Mountain View’s

10.0 out of 10, Exceptional, (130)
"Nice and comfortable "
Warm Welcoming Retreat in Shenandoah w/1 mile of River, Stunning Mountain View’s
NEW! The Hilltop Station
Exterior

NEW! The Hilltop Station

6.0 out of 10, (1)
"A train came past the house at 7am in the morning. There is no mention of early morning train activity in the description. The mattresses were extremely soft and the blankets were very thin…so we were chilly. The house is beautiful…just these details are something to consider."
The price is AED 1,081
AED 2,233 total
includes taxes & fees
29 Oct - 30 Oct
NEW! The Hilltop Station
Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub
Miscellaneous

Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub

10.0 out of 10, Exceptional, (384)
"What a wonderful property! Our stay was restful and quiet, and we were even treated to visiting deer! This lovely home made our visit to the area very special."
Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub
Private Trail To Wine: 5-bedroom Farmhouse In Heart Of Virginia Horse Country
Terrace/patio

Private Trail To Wine: 5-bedroom Farmhouse In Heart Of Virginia Horse Country

9.8 out of 10, Exceptional, (59)
"Despite some early drama around checkin time, we had a great family getaway at this property. Super close to fun wineries & small towns. "
Private Trail To Wine: 5-bedroom Farmhouse In Heart Of Virginia Horse Country
Peaceful Retreat on Creekside
Fridge, microwave, oven, stovetop

Peaceful Retreat on Creekside

9.4 out of 10, Exceptional, (10)
"We liked being out in the country. Loved hearing the sounds of the woods and the farms. Lovely spot"
The price is AED 343
AED 764 total
includes taxes & fees
1 Oct - 2 Oct
Peaceful Retreat on Creekside
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

Courtyard by Marriott Winchester

Courtyard by Marriott Winchester

10/10 Excellent
"Beautiful and comfortable room, which was very quiet and very clean. I would definitely stay here again and would recommend it to anyone. Our only issue was an electrical outlet in the bathroom that did not work. The front desk put in an immediate request for maintenance to fix it. Other than that, it was a perfect day."
Katherine 1-night trip
Posted 3 days ago
Courtyard by Marriott Winchester