Holiday rentals in Stillwater

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Top-rated holiday rentals in Stillwater

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Guest favourite
The exterior of a spacious log home is showcased, featuring a prominent central entry with three large windows above the door. Flanking shrubs with bright yellow blossoms add a vibrant touch. A green lawn surrounds the structure, under a clear blue sky.
Home in Stillwater
4.91 out of 5 average rating, 11 reviews

Saratoga Luxury Log home - track week special!

Gorgeous log home set on 82 acres just 3 miles from Saratoga Lake, 10 miles from downtown Saratoga Springs. Expansive views, private walking trails, and outdoor firepit. Escape, relax in this quiet, private piece of paradise. Stunning views of Equinox Mountain in VT, breathtaking sunrises and sunsets. Guest bedrooms are very large, with lofted high beam ceilings. Great room picture windows and professional kitchen, granite counters Massage Therapy available onsite, complete your dream getaway!

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
4.97 out of 5 average rating, 123 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
Cabin in Shaftsbury
4.99 out of 5 average rating, 327 reviews

The Hygge Loft- mid-mod cabin on 70 acres w/HotTub

The Hygge Loft: a midcentury modern-designed cabin nestled among 70 acres of privately-owned forest with rivers & hiking trails. Enjoy sipping an espresso or wine while listening to vinyl records, cozied up by the wood-burning fireplace. Take a walk in the forest to the river or stargaze by the firepit on the private deck. Indulge in a luxurious bath or snuggle up in the ultra comfy king-size bed with views of treetops and sky all around. It’s the kind of place you’ll never want to leave!

Superhost
The image features a natural scene with a wooden table in the foreground, adorned with a planter filled with vibrant flowers. Beyond, rolling green fields and distant mountains are visible through a border of trees, showcasing a serene outdoor environment.
Tiny home in Cambridge
4.89 out of 5 average rating, 107 reviews

A Bedroom in the woods with lovely views!

Picturesque location on farmland with views of the mountains. We are a micro farm. Wake up and watch the sunrise and go for a short hike on the property, and get to know the animals. We are located 35 minutes from Saratoga Springs and Lake George, NY and 45 minutes from Dorset and Manchester, VT. Hike the Adirondack or Green Mountains, paddle the streams or go to a nearby small city for a play, a festival, or a concert. There is a long list of things to do and see within an hour of us!

Guest favourite
Flat in Stillwater
4.92 out of 5 average rating, 13 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.

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
4.96 out of 5 average rating, 302 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

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
4.89 out of 5 average rating, 123 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! 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
4.92 out of 5 average rating, 51 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

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, 307 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.

Top guest favourite
A covered deck is shown, featuring a black railing that frames a view of the tranquil waterfront. A wooden dock extends into the water, surrounded by greenery, while a quiet road is visible below. Morning light creates gentle shadows across the deck.
Home in Stillwater
4.98 out of 5 average rating, 49 reviews

Harmony on the Hudson Waterfront

Newly updated upstairs waterfront property! Relax and enjoy one of the best views of the upper Hudson from your covered patio or upper deck. Lower level is for private storage only. Property accessible by car or boat. Dock available for fee. Upstairs unit has 2 bdrms with queen beds, one bath and an office with open concept living area. 20 min, SPAC and famous Saratoga Race Track.Self Check in & wifi.

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, 352 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.

Top guest favourite
A wrought-iron archway frames the view of a tranquil lake, leading toward a wooden dock that extends into the water. Flower pots adorned with vibrant blooms sit atop a stone wall, enhancing the serene lakeside atmosphere.
Home in Saratoga Springs
4.97 out of 5 average rating, 119 reviews

Waterfront Saratoga Lake home!- Pool, dock, kayak

My home is close to Saratoga Racetrack, Casino, SPAC, Museums, Dining and Shopping. You’ll love my place because, "We Have It All," Direct Lakefront, 10 x 20 In-ground Pool, Private 100ft Dock, Kayak 's . Pool open Memorial Day to Labor Day.

Popular amenities for Stillwater holiday rentals