Bed and Breakfast in Middletown, NY

Find the best offers in Middletown, NY

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
Middletown, NY bed and breakfast
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

9 Bed and Breakfasts and Inn in Middletown, NY

Best Middletown, NY bed and breakfasts with breakfast included

Buck's Homestead B&b - Middletown, NY
9.6 66 reviews
Middletown, NY
25/06 – 04/07
£190/nighttotal: £1710 (9 )

Buck's Homestead B&b

1 2
B&B , Montgomery
This charming bed and breakfast is situated in Montgomery, just 2.6 kilometres from the City Winery Hudson Valley and 4.5 kilometres from the Orange County Farmers Museum. It has received excellent reviews from previous guests.
The property features a peaceful garden, a terrace or balcony, and free on-site parking. Guests can enjoy a complimentary breakfast and explore nearby attractions like Thomas Bull Memorial Park and the Orange County Arboretum.

Best Middletown, NY bed and breakfasts with a garden

Parkway House Goshen Bed & Breakfast Suite #1 - Middletown, NY
Middletown, NY
21/08 – 23/08
£411/nighttotal: £822 (2 )

Parkway House Goshen Bed & Breakfast Suite #1

1 5
B&B , Goshen
This Bed and Breakfast is located in Goshen's city centre, a 4-minute drive from Legoland New York and near the Goshen Harness Racing Track.
This 900 square meter guesthouse offers one bedroom and one bathroom, accommodating up to six guests, with features including air conditioning, internet, a terrace, and a garden, and is ideal for those seeking a base for visiting local attractions such as the United States Military Academy and the Harness Racing Museum and Hall of Fame.
Parkway House Goshen Bed & Breakfast Suite #4 - Middletown, NY
10 2 reviews
Middletown, NY
21/08 – 23/08
£411/nighttotal: £822 (2 )

Parkway House Goshen Bed & Breakfast Suite #4

1 5
B&B , Goshen
This Victorian Inn is located in the village centre of Goshen, 4 kilometres from Legoland New York, 15 kilometres from Woodbury Commons Premium Shopping Outlets, and offers views of the Goshen Historic Track.
This family-friendly guesthouse provides a spacious 2-bedroom suite with a capacity for six guests, featuring air conditioning and Wi-Fi, with complimentary breakfast served daily.
Parkway House Goshen Bed & Breakfast Suite #2 - Middletown, NY
Middletown, NY
21/08 – 23/08
£463/nighttotal: £926 (2 )

Parkway House Goshen Bed & Breakfast Suite #2

1 5
B&B , Goshen
This restored Victorian inn is located in the centre of Goshen Village, just a 4-minute drive from Legoland New York Theme Park, and offers a 2-bedroom suite with exclusive views of the Goshen Historic Track.
The 800 square meter property provides accommodation for up to 8 guests, featuring air conditioning, Wi-Fi, a terrace, and a garden, with options to rent the entire house, barn, or the whole property, and serving a complimentary gourmet breakfast daily.
Buck's Homestead B&b - Middletown, NY
9.6 66 reviews
Middletown, NY
25/06 – 04/07
£190/nighttotal: £1710 (9 )

Buck's Homestead B&b

1 2
B&B , Montgomery
This charming bed and breakfast is situated in Montgomery, just 2.6 kilometres from the City Winery Hudson Valley and 4.5 kilometres from the Orange County Farmers Museum. It has received excellent reviews from previous guests.
The property features a peaceful garden, a terrace or balcony, and free on-site parking. Guests can enjoy a complimentary breakfast and explore nearby attractions like Thomas Bull Memorial Park and the Orange County Arboretum.

Frequently asked questions about bed and breakfast in Middletown, NY

  • What is the typical weather in Middletown, NY, and how does it affect outdoor plans?

    Middletown has four distinct seasons. Summers are warm and humid, with temperatures reaching around 27 degrees Celsius. Winters are cold and snowy, with temperatures averaging around -3 degrees Celsius. Spring and autumn are mild and pleasant, with temperatures in the mid-teens. You'll want to plan your outdoor activities accordingly, as heavy snow can make some trails inaccessible in winter.
  • What are the best bed and breakfasts in Middletown, NY?

  • What dining options are recommended for solo travelers staying at bed and breakfasts in Middletown, NY?

    There are a few great places for solo travellers in Middletown. The Cornerstone Cafe has a lovely, relaxed atmosphere and is great for a casual meal. If you're looking for something more upscale, The Tavern at the Graymoor offers a refined dining experience with beautiful views of the Hudson River.
  • What are the best bed and breakfasts with a pool in Middletown, NY?

    Mini Cozy Small Room, Beautiful Peaceful Room and Secluded Retreat are the best B&Bs with a pool in Middletown, NY.

  • What are the best cultural activities and events in and around Middletown, NY?

    Middletown has a vibrant cultural scene. The Middletown Arts Center hosts a variety of performances, exhibitions and workshops. You can also check out the Orange County Fair, held annually in July, which features live music, food and entertainment. For a more historical experience, visit the Middletown Historical Society museum.
  • What are the best bed and breakfasts with a jacuzzi in Middletown, NY?

  • Which hiking trails are recommended for exploring in and around Middletown, NY?

    There are some great hiking trails around Middletown. The Minnewaska State Park Preserve offers a variety of trails with breathtaking views of the Shawangunk Mountains. For a shorter hike, try the Wallkill Valley Rail Trail, a paved path that follows the Wallkill River.
  • What are the best bed and breakfasts for families and kids in Middletown, NY?

  • What amenities are commonly offered in bed and breakfasts in Middletown, NY?

    Most bed and breakfasts in Middletown offer basic amenities like a comfortable bed, private bathroom and a continental breakfast. Some also offer additional amenities like a fireplace, hot tub or swimming pool. You'll want to check the specific amenities offered by each bed and breakfast before booking.
  • What are the best pet friendly bed and breakfasts in Middletown, NY?

    The best pet friendly B&Bs in Middletown, NY are Warm Purple Bedroom W/ Free Tv, Upbeat Country Retreat and Private Room Near Touro College.

  • What are the best bed and breakfasts with parking in Middletown, NY?

Destinations nearby

Search B&Bs with Free Parking in Middletown, NY

Make the most of the city centre with a free car park on-site, included with every B&B in Middletown, NY for stress-free arrivals.

Buck's Homestead B&b - Middletown, NY
9.6 66 reviews
Middletown, NY
25/06 – 04/07
£190/nighttotal: £1710 (9 )

Buck's Homestead B&b

1 2
B&B , Montgomery
This charming bed and breakfast is situated in Montgomery, just 2.6 kilometres from the City Winery Hudson Valley and 4.5 kilometres from the Orange County Farmers Museum. It has received excellent reviews from previous guests.
The property features a peaceful garden, a terrace or balcony, and free on-site parking. Guests can enjoy a complimentary breakfast and explore nearby attractions like Thomas Bull Memorial Park and the Orange County Arboretum.
Hudson Valley Horse Farm Stay | 10 Min To Legoland - Middletown, NY
10 6 reviews
Middletown, NY
22/07 – 26/07
£312/nighttotal: £1248 (4 )

Hudson Valley Horse Farm Stay | 10 Min To Legoland

1 2
gîte , Scotchtown
This Scotchtown lakefront apartment, situated approximately 320 kilometres from Manhattan and near Goshen's Heritage Trail and Harness Racing Museum, offers a unique Hudson Valley escape.
The self-contained flat boasts one bedroom, one bathroom, sleeping two guests, and includes a fully equipped kitchen with dishwasher, air conditioning, parking, on-site amenities such as a barbecue, fire pit, and access to canoes and paddleboats, plus three friendly horses on the 7-acre farm.

Best Middletown, NY bed and breakfasts with air conditioning

Private Apartment In Gorgeous Mansion On 8 Acres - Middletown, NY
9.9 27 reviews
Middletown, NY
28/08 – 05/09
£204/nighttotal: £1632 (8 )

Private Apartment In Gorgeous Mansion On 8 Acres

1 3
B&B , Scotchtown
This private apartment in Goshen, New York is just an hour from midtown Manhattan and close to attractions like Woodbury Commons, West Point, and the Hudson Valley Wine Trail. It has received excellent ratings for its location, cleanliness, and overall experience.
The apartment is spacious, accommodating up to four guests, and offers a private entrance. Guests can enjoy a large in-ground pool, a private BBQ grill, and bicycles for exploring the area, as well as a modern kitchen and bathroom.
Charming Upstate New York Inn Cozy Suite #3 - Middletown, NY
10 2 reviews
Middletown, NY
28/08 – 05/09
£117/nighttotal: £936 (8 )

Charming Upstate New York Inn Cozy Suite #3

1 3
B&B , Otisville
This guest house in Otisville, Upstate New York, is situated a short distance from Middletown's shops and attractions, and offers convenient access to outdoor activities such as hiking and visiting local wineries.
This property provides one bedroom and one bathroom for up to three guests, featuring air conditioning, internet access, and an 800 square feet porch, with artful interiors offering items for purchase and a sun-filled lounge.
Parkway House Goshen Bed & Breakfast Suite #2 - Middletown, NY
Middletown, NY
21/08 – 23/08
£463/nighttotal: £926 (2 )

Parkway House Goshen Bed & Breakfast Suite #2

1 5
B&B , Goshen
This restored Victorian inn is located in the centre of Goshen Village, just a 4-minute drive from Legoland New York Theme Park, and offers a 2-bedroom suite with exclusive views of the Goshen Historic Track.
The 800 square meter property provides accommodation for up to 8 guests, featuring air conditioning, Wi-Fi, a terrace, and a garden, with options to rent the entire house, barn, or the whole property, and serving a complimentary gourmet breakfast daily.
Parkway House Goshen Bed & Breakfast Suite #1 - Middletown, NY
Middletown, NY
21/08 – 23/08
£411/nighttotal: £822 (2 )

Parkway House Goshen Bed & Breakfast Suite #1

1 5
B&B , Goshen
This Bed and Breakfast is located in Goshen's city centre, a 4-minute drive from Legoland New York and near the Goshen Harness Racing Track.
This 900 square meter guesthouse offers one bedroom and one bathroom, accommodating up to six guests, with features including air conditioning, internet, a terrace, and a garden, and is ideal for those seeking a base for visiting local attractions such as the United States Military Academy and the Harness Racing Museum and Hall of Fame.
©2026 cozycozy.com