Vacation Homes in Middletown
Wander Wisely with exceptional service, 24/7 support
Save an extra 10% or more on select hotels with Member Discounts
Access exclusive hotel deals, only with the Travelocity app
Featured Vacation Homes in Middletown

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

On the river ~ hot tub ~ serene river views ~ fire pit

Cozy Lakeside Homestead

The Apple Mountain House

Secluded River Cabin Getaway (Masten Cabin)

Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub

Historic Slate Hill School House in Fort Valley, Virginia

Screened Porch w/Swing, Fire Pit, Grill & Deck

Mountain View Bungalow in Front Royal

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

New Charming 3-bedroom townhome with WiFi and AC in Winchester

River Woods Retreat:10min to River, L2 EV, Hikes, 2 Fireplaces, Hottub, SP 10mi
Top trending hotels in Middletown

Comfort Inn & Suites Winchester
Vacation Rentals in Middletown
What kind of vacation do you want in Middletown? The answer to that question will help you choose the right lodging for your stay. The wise wanderer knows that a vacation rental is an essential part of the traveling experience. It’s more than just a place to crash at night—it’s where you wake up in the morning, where you lounge when you’re not exploring, and it’s the starting point for all your adventures. No matter what type of vacation homes strike your fancy, Travelocity has something in Middletown that will speak to you.
Do you want a fully equipped kitchen so you can exercise your culinary mastery and impress your travel buddies? How about a romantic terrace for your anniversary trip? Have you always wished to fall asleep to the sound of waves crashing on the shore? One of our vacation home rentals is bound to add that extra magic to your trip. In fact, we’ve got plenty of options lined up just for you in Middletown, including luxury vacation rentals. On a budget? We can work with your funds and still give you a great place to sleep at night.
Take a look at what we have on offer. You’ll find rentals close to the big tourist draws, as well as rentals that keep you away from the crowd. Consider vacation rentals a little off the beaten path where you can live like a local and discover hidden gems that never make it to the tourist sites. Book through Travelocity and start your getaway today.
Middletown Vacation Homes essential information
Accommodation | 196 Vacation Homes |
---|---|
Lowest Price | CA $110 |
Highest Price | CA $692 |
Popular accommodation | Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly, On the river ~ hot tub ~ serene river views ~ fire pit, Cozy Lakeside Homestead, The Apple Mountain House, Secluded River Cabin Getaway (Masten Cabin), Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub, Historic Slate Hill School House in Fort Valley, Virginia, Screened Porch w/Swing, Fire Pit, Grill & Deck, Mountain View Bungalow in Front Royal, 5-bedroom Farmhouse In Heart Of Virginia Horse Country- Private Trail To Wine, New Charming 3-bedroom townhome with WiFi and AC in Winchester, River Woods Retreat:10min to River, L2 EV, Hikes, 2 Fireplaces, Hottub, SP 10mi |