Middletown vacation rentals

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Top-rated vacation rentals in Middletown

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Guest favorite

Farm stay in New Paltz

4.92 out of 5 average rating, 612 reviews

The 1772 Lefevre Stonehouse Suite

Sit at a quaint breakfast table in this sun-filled room admiring the beautiful patio, grainy wood-plank floors, and a country decor touches. Walk outside to enjoy the rustic grounds of this enchanting stone-built home dating from 1772. The suite has its our private entrance, bathroom and fireplace all stocked with plenty of firewood for your stay. Fireplace can be used November-March only unless temperatures are under 40 degrees. Our home is located just seven minutes from New Paltz and two minute from Gardiner. The property is on 60 acres of rural land that you are welcome to explore. The room includes a queen size bed, a pullout futon for an extra (small) person, mini fridge, microwave and coffee machine. Enjoy your morning coffee on the large stone patio while listening to the roosters crow and birds singing. We raise around 250 egg layer chickens and 800 meat chickens on the property. They Love treats from you. If you’d like they will take snacks right from your hand. The roosters are tame and friendly. We now also have Lucy the goose. She watches over the chicken flock. The rail trail, where you can bring your bike and ride into New Paltz, is only a quarter of a mile away through our property then down a quiet country road. Our home is just minutes from Minnewaska State Park, Mohonk Preserve, and the historic Mohonk Mountain House. The New Paltz area has some of the finest restaurants you can dine at. The Town of Gardiner is only two minutes down the road. There you will find Café Mio and a pizzeria for a quieter dining experience. Gardiner also has Yard Owl Brewery, Gardiner Brewing Company (this is my son and daughters newly opened farm brewery on our main farm property in our old dairy barn), The Gardiner Mercantile and Tuthilltown Spirits each of which are great places to stop in and have a drink and a lite meal. Wright's Farm (Our Farm) is also 1 mile south on 208 features homemade baked goods, local cheeses, fruits and vegetables, fresh from the farm pork and chicken, wine, local spirits, hard cider Gardiner Brewing Company canned beer, bedding plants and fabulous hanging baskets and finally pick your own strawberries (second week in June-end of June), cherries (third week in June-first of July) and apples in September and October. The guest have their own access via private entrance to the bedroom suite , hot tub and the 60 acres. We are farmers and work a lot therefore we are only here early in the morning and after 7 or 8 o'clock at night. At those times we would love to interact with our guest if they are willing. If guest would like to come to our farm we are always here to talk to our guests and if we have time give them a tour of our farm and new farm brewery. Set on secluded grounds, this Historic stone home is situated on 60 acres of land with chickens, ducks and 3 goose as our neighbors. The Hamlet of Gardiner is a 3-minute drive away, and New Paltz is just a bit farther. It’s best if you have a car. There is no public transportation here. You can get a taxi or an Uber from New Paltz. Bring your bikes. The rail trail is only 1/4 mile away. Drive your car into the town of Gardiner and park at the rail trail parking lot. If you are coming by bus you will arrive in New Paltz. From there you will need to take a taxi or Uber to our home. This is a very rural area so please stop at the store prior to your arrival. We do have a supermarket that is 3 miles away and Wright's Farm Market open 8-6 year round that is 1 mile away. If you bring your dog please be a where that you may not leave the dog in the room unattended.

Sep 19 – 26

$123 per night

Guest favorite

Cottage in Monticello

4.92 out of 5 average rating, 130 reviews

Cozy Catskill Getaway Upstate NY - 5 min to casino

Kick back and relax in this cozy styled cottage! Centrally located near shopping plazas including Shoprite, Walmart and Marshalls. Also close to eateries, fast food restaurants, and Resorts World Casino. Explore the Catskills and come back to stay in a warm cottage. Although it is centrally located, it's pushed back enough that you still get the country living feeling. Located on 2 acres of land, you're sure to hear the birds chirping! There is a pull out couch available for an additional guest.

May 1 – 8

$114 per night

Guest favorite

Guest suite in Montgomery

4.95 out of 5 average rating, 419 reviews

Garden View Guest Cottage

Located under 15 min. to Stewart Airport...1 mile to City Winery , nearby Angry Orchards , 1/2 hour to West Point Charming cottage setting located in the village of Montgomery, NY, Come for the day or stay for a few to take in all this historic area has to offer. Walk to some of the best restaurants in Orange County or simply read a book in the gardens... Truly a great value since it's a true "apartment " like setting..not just a room, with all the conveniences and sleeps up to 6 people

Nov 24 – Dec 1

$113 per night

Superhost

Home in Bloomingburg

4.8 out of 5 average rating, 461 reviews

Δ Scenic Hiking Paradise with Deck and Fire Pit!

Relax at this peaceful place atop the Shawangunk Mountain Ridge. You'll enjoy plenty of room at this wooded oasis! • On 2 wooded acres • Beautiful area • Deck off kitchen w nice grill • Lawn fire pit w seating & string lights • Adjacent to 1600 acres of State Forest with official hiking trails & Amazing Views right near house • EXTRA Professional Covid Cleaning • Home gym & treadmill • 3 bedrooms • Large living room with 2 sleeper sofas • Near great outdoor and indoor attractions

May 2 – 9

$123 per night

Guest favorite

Guest suite in Chester

4.95 out of 5 average rating, 230 reviews

Adorable Guest Apartment in Victorian Mansion

This lovely 3rd floor private apartment is in an 1883 Victorian Mansion in Blooming Grove, NY for 1 - 6 people. It is beautifully furnished, and has luxurious beds, so let us know if you need one, two or three bedrooms! The apartment has a private entrance, a claw foot tub, a French door shower, and a kitchenette with sunny breakfast nook. It is freshly renovated and spacious. You will have to take 2 staircases. Our land has a nice view of a field of wildflowers, and our neighbor has cows.

Jan 31 – Feb 7

$92 per night

Guest favorite

Cabin in Wurtsboro

4.98 out of 5 average rating, 201 reviews

Spring Spa on a Cascading Brook - The Water House

The brook flows through an evergreen forest creating a nourishing environment and the perfect setting for a relaxing and rejuvenating spa retreat. The living/dining room, hot tub/deck, and fire pit are set overlooking the cascading brook, ideal for entertaining, meditating or simply as an enjoyable natural muse. The soft, cozy and elegantly vintage styled interior is illuminated and warmed with central heating, ambient lighting and a home surround sound entertainment system with karaoke.

Mar 29 – Apr 5

$259 per night

Guest favorite

Cottage in Goshen

4.94 out of 5 average rating, 193 reviews

Cheery & Peaceful Farm Cottage, 10 Min to LEGOLAND

When you're looking to get away from it all and experience some peace and quiet surrounded in nature, this Cottage fits the bill. Whether it's enjoying fireflies over the field at dusk or enjoying cheerful birds in the morning, this beautiful Cottage sets the stage for you to be refreshed and renewed by the time you check out. While it feels like a secluded oasis, this place is also 10 minutes from LEGOLAND, Target, and all your other favorite conveniences. We look forward to hosting you.

Mar 20 – 27

$116 per night

Guest favorite

Apartment in Warwick

4.95 out of 5 average rating, 151 reviews

THE GEM: In The Heart Of It All!

Enjoy a COZY, CLEAN and NEWLY RENOVATED apartment with an OUTDOOR BALCONY, located in the heart of Warwick! All the great restaurants and shops within walking distance. SPECIAL PRICING FOR MONTH LONG STAYS DURING THE WINTER SEASON. This wonderful apartment comes with a fully equipped kitchen, queen bed, full bath and tub. This apartment has its own entrance and is very PRIVATE. FREE PARKING LOT within walking distance of apartment and WiFi enabled smart TV with a Netflix subscription.

Jul 12 – 19

$136 per night

Guest favorite

Home in Middletown

4.97 out of 5 average rating, 153 reviews

Peace and quiet. Quaint country house to relax in.

Quiet property,almost 8 acres, of beautiful wooded property . Set back from the road. Many trails, wineries and breweries nearby. Legoland is 20 minutes away and many antique shops within 30 minutes or so. We live in the other house on the property, so we are accessible. You can take a stroll on the path by the stream or sit on the spacious 35 x 10 foot deck and enjoy the natural setting of the property. Fire pit is now available. Enjoy the night air and gaze at the stars.

Sep 28 – Oct 5

$188 per night

Guest favorite

Tiny home in New Paltz

4.99 out of 5 average rating, 742 reviews

Hudson Valley Tiny House

If you've been looking for the tiny house experience, look no further. Michelle and Chris built this tiny house to live as eco-friendly, comfy, and healthy as possible. Built with only non-toxic and all natural materials with a state of the art fresh-air system. Enjoy wildlife or relaxing at the river bend on our 5-acre property or explore the awesome attractions close by: county pool, winery, New Paltz downtown, “gunks” rock climbing, Minnewaska State Park, and more!

Jul 13 – 20

$95 per night

Guest favorite

Apartment in Chester

4.96 out of 5 average rating, 333 reviews

Luxury Apt/Sugar Loaf/10 Min To LEGOLAND

This lovely modern space was just built in 2015. The space is located in the quaint Hamlet of Sugar Loaf, New York Artisan Village, which is surrounded by the town of Warwick and Chester with Greenwood Lake just minutes away...and NYC is just 75 minutes. It's a second floor apartment with private front and back entrances. Rear deck overlooks spacious fenced in yard with pond view. Walking distance to 2 restaurants and deli. LEGOLAND just 8 miles!

Apr 14 – 21

$141 per night

Guest favorite

Home in New Paltz

4.97 out of 5 average rating, 677 reviews

Victorian Haven

Victorian Haven is located near the Shawangunk Mountains that extends for over 20 miles and reaches 2,200 feet in height at Sam's point, the highest elevation on the ridge. In addition, the Wallkill River provides unspoiled and picturesque spots for hiking, fishing and/or picnics. Gardiner has a beautiful rail trail that follows the path of the 1860's railroad and provides a great opportunity to hike, bike or ski.

Dec 31 – Jan 7

$115 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Middletown vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Middletown's top sights

Orange County Fair Speedway9 locals recommend

IHOP4 locals recommend

ShopRite of Middletown12 locals recommend

ALDI3 locals recommend

DeStefano's Olde Erie3 locals recommend

Saffron3 locals recommend

Other great vacation rentals in Middletown

Guest favorite

Condo in Vernon Township

4.97 out of 5 average rating, 144 reviews

Comfy Studio at Mountain Creek Resort

Jan 16 – 23

$90 per night

Guest favorite

Cabin in Kingston

4.98 out of 5 average rating, 332 reviews

Come Stay in "The Shoe"

Feb 9 – 16

$115 per night

Guest favorite

Home in Napanoch

5.0 out of 5 average rating, 158 reviews

Cozy Home on the Hill (Welcome to the country!)

Apr 21 – 28

$126 per night

Guest favorite

Guest suite in Haverstraw

4.95 out of 5 average rating, 293 reviews

Haverstraw Hospitality Suite

Apr 18 – 25

$74 per night

Guest favorite

Cabin in Vernon Valley

4.97 out of 5 average rating, 344 reviews

Serenity Cabin, the historic waterfall cabin!

Aug 22 – 29

$154 per night

Guest favorite

Guesthouse in Peekskill

4.94 out of 5 average rating, 206 reviews

Peekskill Carriage House Downtown Studio

Oct 28 – Nov 4

$114 per night

Guest favorite

Apartment in New Paltz

4.96 out of 5 average rating, 346 reviews

Modena Mad House

Oct 8 – 15

$114 per night

Guest favorite

Loft in Warwick

4.96 out of 5 average rating, 205 reviews

Luxe Loft 1 Warwick on Main St, SteamShower,Views!

Jul 28 – Aug 4

$162 per night

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Other great vacation rentals in Middletown

Guest favorite

Apartment in Newburgh

4.93 out of 5 average rating, 213 reviews

ECO MCM GEM- central to Bethels & West Point

Jul 18 – 25

$115 per night

Guest favorite

Guest suite in New Paltz

4.89 out of 5 average rating, 832 reviews

Cozy New Paltz apartment (no cleaning fee)

Oct 30 – Nov 6

$80 per night

Guest favorite

Home in Kingston

4.97 out of 5 average rating, 276 reviews

This New House

Mar 6 – 13

$125 per night

Superhost

Apartment in Middletown

5.0 out of 5 average rating, 7 reviews

Cozy Studio Retreat in the Heart of Middletown

May 12 – 19

$63 per night

Guest favorite

Guesthouse in Middletown

5.0 out of 5 average rating, 10 reviews

Hudson Valley Retreat on 8 Acres

Sep 21 – 28

$156 per night

Guest favorite

Home in Montgomery

5.0 out of 5 average rating, 7 reviews

Escape to serenity at the Pullman Cottage

May 4 – 11

$108 per night

Guest favorite

Cottage in Middletown

4.93 out of 5 average rating, 46 reviews

Hello Small Stone

May 6 – 13

$144 per night

Guest favorite

Cottage in Middletown

4.96 out of 5 average rating, 48 reviews

⌂ Backyard Porch ⌂ Cozy Getaway ⌂ Catskills Hikes

Jun 7 – 14

$181 per night

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Quick stats about vacation rentals in Middletown

Total rentals
40 properties
Wifi availability
40 properties include access to wifi
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
650 reviews
Nightly prices starting at
$40 before taxes and fees

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Middletown?
Yes! Work meets play with ease at over 20 vacation rentals in Middletown featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in house rentals in Middletown?
Experience the best of Middletown with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Middletown have wireless internet?
Absolutely! We offer over 20 house rentals with wireless internet in Middletown. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Middletown?
Middletown has more than 10 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Middletown have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Middletown. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Apartment Rentals in Middletown?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wireless internet, and more. Indulge in the ultimate retreat, tailored to your preferences.

Middletown vacation rentals

Top-rated vacation rentals in Middletown

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Middletown vacation rentals

Stay near Middletown's top sights

Other great vacation rentals in Middletown

Condo in Vernon Township

Cabin in Kingston

Home in Napanoch

Guest suite in Haverstraw

Cabin in Vernon Valley

Guesthouse in Peekskill

Apartment in New Paltz

Loft in Warwick

Other great vacation rentals in Middletown

Apartment in Newburgh

Guest suite in New Paltz

Home in Kingston

Apartment in Middletown

Guesthouse in Middletown

Home in Montgomery

Cottage in Middletown

Cottage in Middletown

Quick stats about vacation rentals in Middletown

Total rentals

Wifi availability

Rentals with dedicated workspaces

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Middletown?

How much does it cost to stay in house rentals in Middletown?

Do house rentals in Middletown have wireless internet?

Are there family-friendly house rentals in Middletown?

Do house rentals in Middletown have air conditioning?

What are the most popular amenities for Apartment Rentals in Middletown?

Destinations to explore