Holiday rentals in Town of Milan

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Town of Milan

Guests agree: these stays are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

Top guest favourite

Guest house in Rhinebeck

4.99 out of 5 average rating, 128 reviews

Country Suite Near Omega Inst and Rhinebeck

We designed our guesthouse with the comfort seeking guest in mind. Enjoy our extra comfy plush beds, soft and fresh bed linens, luxurious towels, and complimentary essential oil infused bath amenities for your ultimate getaway. Complimentary snack and beverage selections provided for your enjoyment in our efficient kitchenette which can accommodate light meals. Our second floor guesthouse offers a newly installed ductless HVAC to provide the ultimate comfort air-conditioning or heating as needed. Many of our guests comment on our relentless pursuit of cleanliness. Some features included are: kitchen with microwave, toaster oven, refrigerator/freezer, electric tea kettle, and Keurig coffee maker. Also, oversized shower, dimmable lighting, keyless access, internet, smart TV, blackout window treatments, heating and air conditioning. Kitchen is for light meal preparation only, no stove. Complimentary snacks, beverages, and bath amenities provided. Echo Dot with Amazon Alexa in suite for guest use. Please note: entrance includes one flight of stairs to enter and exit the country suite. Available promptly by Airbnb messaging, text or phone for any questions or needs during your stay. The guesthouse is within walking distance to the Omega Institute for Holistic Studies, 8 miles to the charming and historic town of Rhinebeck, and central to many pursuits in the Hudson Valley. Walk or run around the lake for a 3.5-mile outing. 90 miles from NYC along Taconic State Pkwy. 15 mins from Amtrak's Rhinecliff station. 25 mins from Metro North's Poughkeepsie station. Walk or run around the lake for a 3.5 mile outing. Our guesthouse is a separate structure from our main home on the property. Each building is separated by around 30 feet.

Top guest favourite

Cabin in Red Hook

4.96 out of 5 average rating, 363 reviews

Modern Upstate Cabin, near Rhinebeck NY

[ 🏊🏽‍♂️ Heated pool is open May - October 26, 2025. During the colder months we recommend soaking in our giant freestanding tub, which easily fits two humans.] Welcome to Maitopia - our modern, tiny cabin in the middle of a forest. We offer a fully stocked kitchen, a giant bathtub for two, a floating fireplace for cozy winter moments and a heated pool. Plus, a fenced in yard for your pup to roam! Please note: Because of bad experiences we don’t accept bookings from guests without reviews.

Guest favourite

Cottage in Rhinebeck

4.93 out of 5 average rating, 297 reviews

Ridgetop 2 Br Cabin- Views, 130acre forest & falls

Newly renovated private cabin on the ridge top of an 130 acre magical property with stunning western views and overlooking a historic farm & crystal clear lake. Explore the hiking trails, dip in the wading pools of the upper cascades, bike to town or simply enjoy the peaceful sounds of the 90ft waterfall on the property. Relax in a beautifully designed private retreat, complete with a gourmet kitchen, cozy fireplace, comfortable bedrooms & quiet workspaces- learn more at cascadafarm.com

Top guest favourite

Guest house in Stanfordville

4.93 out of 5 average rating, 186 reviews

Eco Cottage in the Woods

The cottage is light and airy, surrounded by forest. You may see birds and deer from the bedroom or living room. The queen bed is divided from the living room by a bookcase wall. There is a sofa bed in the living room which faces a patio overlooking the woods. We have a 16x36 unheated gunite pool, professionally maintained. The cottage works well for a couple or a couple with children. 2 night minimum required. Pets welcome. Pet owners passing through may stay 1 night.

Guest favourite

Cabin in Pine Plains

4.96 out of 5 average rating, 246 reviews

The Upstate A - Modern Luxury in the Hudson Valley

The Upstate A is a 3 bedroom + sleeping loft, 2.5 bathroom A-frame set on a quiet cul-de-sac in the heart of the Hudson Valley. Built in 1968, it was fully renovated in 2020-2021. Staying here you’ll experience a cozy yet modern vibe, immersed in nature but with all the accoutrements of an upscale stay. You'll find great hiking in the summer, skiing in the winter, fresh upstate air year-round and serenity all day and night. See for yourself: check us out on IG @upstate_aframe

Top guest favourite

Cottage in Rhinebeck

4.93 out of 5 average rating, 166 reviews

Intimate Cottage on Private Estate

Bulls Head Cottage is a thoughtfully-designed retreat nestled within a 2.5 acre estate 5 minutes from Omega Institute and 10 minutes from the charming Village of Rhinebeck. The 720 square foot guest cottage is a relaxing place for up to 2 guests, offering cozy indoor and outdoor space including an office overlooking the property's pond. Enjoy quick access to hiking, shopping, fine dining and more. Under 2 hours from New York City by car or train. Pets not typically allowed.

Guest favourite

Cottage in Rhinebeck

4.88 out of 5 average rating, 200 reviews

Secluded peaceful loft in barn by woods

La Barn Bleue sits on top of a hill by a forest, in a secluded and peaceful property. The main house, where we live is 150 feet down the hill. The apartment sleeps up to 4 people. The bedroom/lounge loft has one king bed and 2 twin beds. Ideal for families and kids above 5 years old. Because we use a rope railing, we cannot host kids under 5 years old for security reasons. We offer Wifi, AC/heat split unit, outdoor Picnic table, bbq, petanque court and pool!

Guest favourite

Home in Rhinebeck

4.96 out of 5 average rating, 186 reviews

Honeybug Snug near Omega Institute!

Welcome to the Honeybug Snug! Now with AIR CONDITIONING : ) The Snug is perfect for a family of 4 or 4 close friends. : ) We still have a little work to do on her and you get to watch her grow. Your comments will be taken to heart, as your comfort is our priority! We live right next door if you need anything : ) We are .9 miles for The World Renowned Omega Institute -Center for Holistic Studies. Less than 15 Minutes to Downtown Rhinebeck.

Top guest favourite

Cottage in Red Hook

4.98 out of 5 average rating, 682 reviews

bright serene + spacious barn @barn and bike

a bright serene space built by locals on the property we live on. we are in what we think is the most beautiful region of the Hudson River Valley - surrounded by pastoral beauty and dramatic landscapes. quaint yet cultured towns in all directions. please read the entire description & rules before booking • beyond 2 guests, the rate adds 50$/night/per person • please add dogs (2 max. 50$/per dog) when booking • we look forward to having you here!

Top guest favourite

Flat in Rhinebeck

4.92 out of 5 average rating, 133 reviews

Private Studio Close to Downtown Rhinebeck

This modern studio apartment is ideal for a weekend retreat or remote working base. Just 17 minutes from Omega, we offer a Queen-size bed, free WiFi, and a Smart TV. The fully-equipped kitchenette and work/eating bar make meal prep and productivity easy. The bathroom features a rain shower head and Bluetooth speaker. With its own entrance and ample street parking, it ensures privacy and convenience. Give it a try – you won’t be disappointed!

Top guest favourite

Home in Rhinebeck

4.98 out of 5 average rating, 164 reviews

Long Pond Cottage, Country Retreat in Rhinebeck

Nestled down a quiet, country road, you’ll find this charming, idyllic retreat. Less than 15 minutes from the village of Rhinebeck, Long Pond Cottage captures the best of the Hudson Valley. This two bedroom, one bathroom Victorian sits on just under an acre of land, offering ample outdoor space to enjoy the warmer months, and is the perfect cozy spot when the weather turns colder. Self check-in at 4pm and check-out 11am. Pet friendly.

Guest favourite

Home in Rhinebeck

4.92 out of 5 average rating, 243 reviews

Rhinebeck Home with an amazing outdoor space+H/tub

Primary bedroom has a king size bed, bathroom, flat/smart TV. Second bedroom has a queen size bed, TV/den has a CB2 modern sofa that extends into a queen size bed. Our house comfortably sleeps 5, with a fireplace, 2 baths, spacious outdoor deck that has screen doors to open or close with a hot tub and bbq. 8 Minutes to historic Rhinebeck, 12 minutes to Red Hook. Bard College, CIA & Omega Institute within reach!