Vacation rentals in Baltimore

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Top-rated vacation rentals in Baltimore

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

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Top guest favorite
Adirondack chairs and a small side table are positioned on a spacious deck, offering an unobstructed view of Okemo resort. The winter landscape features snow-covered ground, complemented by a clear blue sky and distant mountain views.
Home in Ludlow
4.99 out of 5 average rating, 122 reviews

Stunning Okemo Views - 3BD 3BA on 10 Private Acres

Recently constructed on ten private acres with captivating views of Okemo. Three BR, three full bath, air conditioned modern chalet, just 1.5 miles from downtown and 3 miles from Okemo’s base areas. Epic views of Okemo and surrounding mountains from every room. Cozy around the fireplace in the living room or enjoy smores outside by the firepit, or unwind on the deck. Lower level has second living room great for kids with large TV, comfy couches, Pac Man arcade, foosball and board games.

Top guest favorite
The treehouse stands elevated among tall trees, featuring a warm wooden exterior and large windows that allow natural light to fill the interior. A deck extends from the structure, leading to a fire pit area surrounded by gravel.
Treehouse in Putney
4.99 out of 5 average rating, 160 reviews

Treehouse Haven in Putney-All Seasons

Peaceful, private & fully equipped four-season treehouse, surrounded by nature. ☽ Private & secluded ☽ Central to activities & necessities ☽ Firepit, pellet stove, deck, grill & fully stocked kitchen ☽ Scrupulously clean, unscented products ☽ Clean composting outhouse ☽ Tea & local coffee ☽ Hot outdoor shower-Closed Nov-April ☽ 45min to ski resorts ☽ Swimming holes & hikes ☽ WiFi & electricity Retreat from the business of life; romance, with the family, or even a remote work sanctuary.

Guest favorite
A recently renovated property is set against a backdrop of lush greenery, featuring a well-maintained lawn and blooming flower beds. The exterior showcases a gray siding, with several large windows allowing natural light into the inviting interior.
Guest suite in Brownsville
4.89 out of 5 average rating, 141 reviews

Newly renovated private space on Ascutney Trails

Newly renovated private space on Ascutney trails--walking distance Ascutney Outdoors Center, hotel, Maple Kitchen Restaurant, skiing, and Brownsville Butcher & Pantry. Trail access in back yard with miles of hiking, mountain biking, running and skiing. Parking for 2 cars. Close to Woodstock shops and Okemo adventure center. Private keycode entrance with self-check in. Microwave, refrigerator, Keurig, coffee and tea provided. Air conditioned during the summer. Television and fast wifi.

Top guest favorite
The private guest house is surrounded by lush greenery, featuring a covered porch with a chimney and hanging planters. A well-maintained lawn leads to the house, while a backdrop of rolling hills enhances the tranquil setting.
Cottage in Windsor
4.97 out of 5 average rating, 428 reviews

Ogden's Mill Farm

Private guest house situated on over 250 acres, with fully equipped gourmet kitchen and great views of quiet fields and valley. Pond with diving board for swimming in the summer. Giant sledding hill is a favorite of children and adults alike. Trails on property for hiking, xc- skiing, and snowshoeing. 15 mins to Woodstock VT. 45 mins to Killington,Pico and Okemo. Great restaurants and shopping nearby. Hanover and Norwich VT 20 mins. Please note not handicapped accesible.

Guest favorite
The exterior of Bearfoot Cottage is highlighted, featuring a combination of wood and metal finishes. A spacious deck with steps leads to the entrance, framed by large windows. A fire pit sits nearby, complemented by comfortable seating arrangements on the gravel surface.
Tiny home in Chester
4.97 out of 5 average rating, 163 reviews

Bearfoot Cottage: Tiny House w/ Hot Tub near Okemo

Tiny living at its best! Welcome to Bearfoot Cottage, a custom-designed Tiny House escape nestled on 15 acres in Southern Vermont. Enjoy the entire property to yourself with hot tub, Char-Griller BBQ, & Solostove firepit. Hike or snowshoe Ladybug Trail to our babbling brook. Then explore the best of Okemo Valley all at your fingertips! Ski/Snowboarding (+more Winter sports), biking, hiking, fishing, dining, breweries, and live music/nightlife. Your vacation is what you make it!

Top guest favorite
A cozy living area features a mixture of seating options, including a tufted sofa and a vintage-style sofa adorned with decorative cushions. Natural wood floors enhance the warmth of the space, while artwork on the walls and a circular coffee table complete the inviting atmosphere.
Barn in Chester
4.99 out of 5 average rating, 705 reviews

Inviting studio apartment above barn in Vermont

This custom build apartment is located just 10 minutes from I91. In the winter you are 30 minutes away from some of the best skiing around. Located on 85 private acres with great views this is the perfect winter get away. In the summer you can relax by the firepit, hike in the woods, work in the gardens (just kidding), collect breakfast from the chickens or visit some of the local breweries. I am as close or as far away as you would like me to be with my house right next door.

Top guest favorite
A well-appointed bedroom showcases a spacious bed dressed in white linens, complemented by decorative pillows. A wooden bench is situated at the foot of the bed. A large mirror and artful wall decor enhance the serene atmosphere, while natural light enters through a large window.
Home in West Windsor
4.98 out of 5 average rating, 162 reviews

Birdie's Nest Guesthouse

Welcome to our newly renovated studio apartment, nestled among the trees in the serene hills of West Windsor, Vermont. Elevated on the second floor, this separate structure offers a tranquil escape with breathtaking views of Mount Ascutney and our own private pond. Immerse yourself in the comforts of this thoughtfully designed studio apartment, surrounded by the natural beauty of the Vermont landscape. Every detail has been curated to ensure your utmost comfort and enjoyment.

Top guest favorite
The exterior of a modern blue house is depicted, featuring a combination of angular roofs and large windows allowing for ample natural light. A stone wall borders the property, which is surrounded by lush greenery and trees in the background.
Apartment in Weathersfield
4.99 out of 5 average rating, 183 reviews

The Loft at Weathersfield

Close to Okemo, The Loft at Weathersfield, is just 1/2 hour south of Woodstock / Hanover area and 22 minutes from Okemo Mountain. The Loft, is located in a private agricultural setting with easy access to Vermont's best biking, hiking, fly fishing, skiing, and many equine trails. The loft is 900 square feet with a kitchen/dining room, living room, full bath, one bedroom with a queen bed and one twin bed. There is a spacious deck off the kitchen and a car port underneath.

Top guest favorite
A welcoming storefront features a wooden sign for Simon Pearce, accompanied by colorful pumpkins and vibrant yellow mums. The gray building showcases a green roof and large windows, with outdoor seating available on the patio. A blue sky with scattered clouds serves as the backdrop.
Apartment in Chester
4.93 out of 5 average rating, 148 reviews

Lovely 2 Bedroom Apartment w/deck & pond view

The perfect Vermont getaway. Lovely new apartment behind retail store on main road to Okemo and Killington for winter skiing and summer adventure. Bedroom, living room, bunk room, fully equipped kitchen, laundry and mudroom. Large deck with pond view, easy access to vacation sites, mountain hiking and biking, discovering Vermont small towns. Experienced, welcoming Airbnb Super Hosts providing all the amenities for a comfortable stay.

Top guest favorite
A spacious living area features a large, yellow sofa paired with a circular coffee table. Two comfortable chairs in rust color are positioned nearby. A vintage-style stove is present against the wall, with soft lighting provided by wall sconces. A door leads to another room.
Guesthouse in Proctorsville
4.96 out of 5 average rating, 177 reviews

Charming Cavendish Guesthouse

Cavendish Cottage Guest House! Freshly renovated with designer touches, this charming guest house blends style, comfort, and Vermont charm. Starting Fall 2025 (date tbd), enjoy free access to our traditional sauna — shared with two other units and your host. Plush robes provided so you can unwind after skiing or hiking, then cozy up by the pellet stove. 10 minutes to Okemo, 2 minutes to groceries, and super comfy vibe await!

Top guest favorite
A historic stone house is surrounded by a blanket of snow, with a steeply pitched roof and charming gables. Large windows reflect the clear blue sky, while the front yard features neatly arranged snow-covered pathways and small evergreen shrubs.
Home in Cavendish
4.95 out of 5 average rating, 109 reviews

VT Retreat: Hot tub | pool table | 70” TV | bbq

Come and stay in this extraordinary Cavendish home filled with historical charm yet fully updated with all the modern amenities you have come to expect. Our home has everything you need for your getaway. Gourmet kitchen, BBQ, Hot Tub, 2 master suites, games room, pool table, 70" TV, and window A/C's in all the bedrooms. Located just a short drive to many of Vermont's summer and winter attractions.

Top guest favorite
A patio area is visible, featuring a stone fire pit with colorful glass accents. Comfortable seating is arranged around the fire pit, with a large umbrella providing shade. The expansive green landscape stretches in the background, offering a view of distant mountains under a cloudy sky.
Apartment in Weathersfield
4.97 out of 5 average rating, 144 reviews

Cute VT Bungalow With 180 Degree View of NH

Located on a quiet country dirt road you will find this cozy apartment perfect for a weekend getaway. A short walk and you will be amazed at the 360 degree views of Vermont and New Hampshire. Centrally located near Okemo, Sunapee and Killington mountains, ski all 3 mountains in a weekend. Explore covered bridges, walking trails, scenic bike rides, or tubing on the Connecticut River.

Popular amenities for Baltimore vacation rentals

  1. Airbnb
  2. United States
  3. Vermont
  4. Windsor County
  5. Baltimore