Holiday rentals in Stillwater

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Top-rated holiday rentals in Stillwater

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Top guest favourite
A spacious bedroom features a large bed adorned with a patterned blanket and decorative pillows. A vintage dresser and a side table are positioned near the bed, while a floral sofa adds a cozy touch. A colorful artwork hangs above, and a rug enhances the warm atmosphere.
Guest suite in Saratoga Springs
4.96 out of 5 average rating, 106 reviews

Charming Saratoga Getaway

Charming Saratoga Getaway: Perfectly Located Escape to a cozy retreat in Saratoga Springs, where charm meets modern comfort! Just 6 minutes from the track by car & 2 minutes from top restaurants, you’ll enjoy the perfect balance of convenience & relaxation. Thoughtful touches, modern amenities, & attentive hosts ensure an exceptional stay. Whether you’re here for the races or to unwind, this serene spot promises lasting memories. No detail is overlooked in this charming, upscale place to stay.

Top guest favourite
A historic Victorian mansion stands gracefully, showcasing intricate architectural details and multiple gabled roofs. A flowering tree adds a natural touch in the foreground, while soft lighting emanates from the windows, creating a welcoming ambiance in the evening.
Flat in Saratoga Springs
4.98 out of 5 average rating, 242 reviews

Saratoga Gem

This lovely apartment is on the second floor of an 1873 Victorian mansion on the North side of town. Very conveniently located about halfway between downtown and Skidmore College. This clean, quiet, owner-occupied house has 2 other apartments. The classic Saratoga front porch, sunny patio in back, and small yard are shared with the host. Kitchen has a small cafe table, dishes/utensils, dishwasher. Bathroom has a deep tub/shower, you’ll have to lift your knee to step in. Memory Foam mattress.

Guest favourite
Flat in Stillwater
4.8 out of 5 average rating, 5 reviews

*New Prelaunch Pricing | River Views Porch Firepit

Welcome to our eclectic river-view retreat! This freshly styled 3-bedroom, 1-bath apartment is the perfect Upstate escape. Whether you’re here for a weekend getaway or a local event, enjoy your own private entrance, a breezy screened-in porch overlooking the backyard, and relaxing views of the Hudson River. With creative touches throughout, this vibrant space offers charm, comfort, and a peaceful vibe—ideal for couples, families, or small groups looking to unwind and explore the area.

Top guest favourite
A bright living area features a plush teal sofa with a chaise, complemented by a decorative floral pillow. A bar stool is positioned near a small kitchen, showcasing stainless-steel appliances and a minimalist design, with natural light streaming through the skylight and windows.
Cottage in Saratoga Springs
4.97 out of 5 average rating, 287 reviews

The Garden Cottage

This is a bright and airy carriage house located on the second floor in a quiet walkable neighborhood. Living room has a drop down movie screen, brand-new sofa with chaise and pull out queen sized bed. Galley kitchen is new with a Smeg stove and oven, dishwasher. Bedroom has a queen size adjustable bed, 52 inch TV with wifi and cable. The bathroom has a soaking tub and a walk in shower a vanity with double sinks. There is a laundry room with a washer and dryer, Owner is a Realtor

Top guest favourite
The spacious living area features large windows that allow natural light to fill the room. Two comfortable couches are positioned around a glass coffee table. A dining table seating six is visible in the background, adjacent to a well-equipped kitchen.
Flat in Saratoga Springs
4.9 out of 5 average rating, 326 reviews

Farm Getaway w/ Pets • Mins to SPAC & Track

Come visit a most peaceful and serene setting as you relax in our fully furnished farm apartment! We have everything you need for a very comfortable stay in Saratoga Springs, NY! Just 12 mins from Saratoga Race track, SPAC, the casino and downtown shopping. You're close enough to dive into the fun yet far enough to unwind. Perfect for a fall getaway. Comfortably sleeps 4 adults with one bedroom and one pull out couch. Full kitchen and beautiful walk out deck to watch the sun rise.

Guest favourite
A lakefront view showcases a multi-story townhome surrounded by lush greenery. A private dock with seating is visible along the shoreline, leading toward the calm waters of Saratoga Lake. Steps descend from the property to the water, enhancing easy access.
Townhouse in Saratoga Springs
4.88 out of 5 average rating, 120 reviews

Saratoga Lake Front #1, minutes to The Track!

Delightful 3,000 sqft lakefront town home only 15 minutes to the historic Saratoga Springs Track and cultural center, on the east shore of the lake, 3 miles to Brown's Beach. Beautiful and spacious rooms with custom finishes. Cozy fireplace to conquer the cold weather! An amazing place to enjoy the gorgeous sunsets from the private wrap around porch! The driveway can accommodate 3 cars. Snowshoes in the closet for your use! NEW: 12' indoor shuffleboard table for hours of fun!

Guest favourite
A light and airy living space is visible, featuring a comfortable sofa paired with a wooden coffee table. An open layout leads to a dining area with a wooden table and chairs. Modern kitchen appliances are seen in the background, enhancing the updated ambiance.
Home in Saratoga Springs
4.95 out of 5 average rating, 43 reviews

Adorable house near lake

Home has recently been updated. Nautical theme cozy house. Come relax on the front porch with views of the lake. In addition to the two bedrooms, there is a loft that has a bed and a desk. Charming and peaceful neighborhood near the lake. Although we don’t offer lake access- our home is 1/2 mile away from Brown public Beach, minutes from some great restaurants, and a few blocks away from the marina where you can rent kayak. Home has fenced yard and doggy door

Top guest favourite
An inviting outdoor space features colorful chairs surrounding a fire pit, set against a winter backdrop. A cozy seating area on a deck showcases modern decor, including a patterned throw and a view of rolling hills framed by an oversized circular window.
Cottage in Shaftsbury
4.98 out of 5 average rating, 765 reviews

Schoolhouse Spa Retreat on a Vermont Farm

Escape to our historic and lovingly-renovated schoolhouse on a 250-acre verified-regenerative farm, where Green Mountain views meet modern comfort. Unwind in your private hot tub and barrel sauna after exploring farm trails, then fall asleep to the gentle sounds of sheep grazing in the pastures below. This is Vermont at its most authentic—working farm life with all the luxury. Level 2 EV charger, in-unit washer/dryer, and ductless AC for summer comfort.

Top guest favourite
The spacious bedroom features a king bed adorned with a dark blue throw and neatly arranged towels. Soft lighting is provided by bedside lamps on each side of the bed, while a plant adds a touch of greenery. Two landscape artwork pieces hang above the bed.
Townhouse in Clifton Park
5 out of 5 average rating, 252 reviews

Cozy Stay – King Bed, Soaking Tub & Fire Pit

Cozy winter reset in Clifton Park—perfectly located for easy trips to Saratoga Springs, Albany, Troy, and Schenectady. Sink into a plush king bed, unwind in the soaking tub, and end the day by the fire pit under string lights. Whether you’re here for a quiet getaway, work trip, or a longer stay, you’ll have comfort, privacy, and the space to truly relax. Outdoor movie screen: “available weather-permitting” + two 65" TV indoors for winter nights.

Superhost
A warm living area features an orange leather sofa paired with a dark ottoman. A modern light fixture hangs from the ceiling, while an open kitchen with stainless steel appliances is visible in the background. Wooden flooring contributes to the cozy atmosphere.
Flat in Mechanicville
4.91 out of 5 average rating, 298 reviews

Boho hipster penthouse - Artsy City vibes upstate!

You are going to love this place!!! It extremely unique and charming!!! 100 Year old school building converted into luxury apartments! The unit you’re viewing is on the MEZZANINE LEVEL, it’s exclusive to you! The unit overlooks the old gymnasium which Has been converted - It’s One of a kind!! A covered roof top terrace, a outdoor patio with fire pit & bbq. Theres a fitness area (Actual registered FALLOUT shelter of the 60’s) to name a few.

Guest favourite
Silhouettes of horses can be seen walking across a grassy area, framed by a wooden fence. A soft morning fog hangs in the air, with the sun rising in the background, casting a gentle light over the scene.
Home in Saratoga Springs
4.8 out of 5 average rating, 177 reviews

NEW 3 bedroom - Thoroughbred Farm & Lake Views!

Great for families with children! Swimming access on Saratoga Lake, and hammock, kayak's, and canoe. Charcoal grill, large entertainment center with CD's, DVD's and Blue-Rays, flat screen TV, dishwasher, washer/dryer. Just minutes away from hiking and biking trails at Luther Forest, Saratoga Track, Saratoga Racino, SPAC, Brown's beach on Saratoga Lake; Only a 5 minute drive!

Top guest favourite
A white farmhouse-style structure is set on a lush green hill, surrounded by a clear blue sky. The building features a gabled roof, multiple windows, and a small cupola. A neat lawn frames the house, emphasizing its inviting exterior.
Home in Bennington
4.99 out of 5 average rating, 343 reviews

Cozy Modern Sugar House with spectacular views.

This beautiful Vermont home sits on 25 acres with spectacular views. We moved this sugar house structure to this land and had an architect adapt it to its surroundings. It has three walls of windows that display the amazing views. The house is surrounded by Mount Anthony hiking trails and a gorgeous pond. The location is a 5 minute drive to town or a lovely 20 minute walk.

Popular amenities for Stillwater holiday rentals

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