Vacation rentals in Bear Mountain

4.99 out of 5 average rating, 138 reviews

Apartment in Pittsford

Waterfront cottage walk-out suite.

Private entrance suite overlooking Burr Pond. Conveniently close to Mountain Top Inn & Resort (3.7 miles), Killington/Pico ski resorts and Rutland. Swim, kayak, bike and hike. Take advantage of more than 12 miles of the Pittsford Trail Network. The serenity of country living coupled with the amenities of Rutland! We’re on a short dirt road off of a steep hill. Front or 4 wheel drive vehicles with good all season or snow tires required in the winter. Not suitable for toddlers or young children.

4.93 out of 5 average rating, 107 reviews

Condo in Mendon

Hotel Chic - Home Comfort -Ski Easy.

HOTEL CHIC - SKI EASY Elegant - Cozy - Spotless Our condo is located minutes from Pico & Killington, 🥾AT&LT, 💍wedding venues, 🚴‍♀️mountain biking, ⛳️golf and many local events. Superhost level comfort welcomes you! OUR ULTRA COZY RETREAT WAITS JUST FOR YOU ⛷️Pico -5 minutes ⛷️Killington -15 minutes 🥾Minutes from LT/AT •Squeaky Clean •Fireplace, TV, WIFI •Seasonal Pool(towels provided) •Private covered porch •Keypad check in •Smoke free/Pet free NOTE: Condo regs allow 2 adults(21yrs)

4.91 out of 5 average rating, 168 reviews

Apartment in Plymouth

Canyons Unit: 1 mile to F&W Summer Camp w/ HOT TUB

The Canyons Unit is a freshly renovated, fully separate, ground level, 2 bedroom apartment in our four-family French Chalet. We are 1 mile to lakes and summer camps and 2 miles from Killington’s Skyeship Gondola. It is 15 minutes from Killington’s main base area and 20 minutes to Okemo. If this listing isn’t available for your interested vacation dates, check out our sister listing called the Moguls Unit. We also have larger 4 bedroom units (The Ledges and Glades) at this same location too.

4.95 out of 5 average rating, 233 reviews

Walk/Bike to Snowshed Lift 2BR @ Mt. Green Resort!

Our CLEAN & SPACIOUS 2 Bedroom and 1.5 Bath Condo is a corner unit in the 4 Season Mountain Green Resort which is located directly across the street from the Snowshed Base Lodge at Killington Mountain (just a 10 minute walk or 2 minute shuttle ride to the slopes) and right next door to the Killington Golf Course. With our recently updated kitchen, renovated master bathroom, luxury vinyl flooring and new furniture, you are sure to enjoy our home away from home in the Green Mountains!

Guesthouse in Wallingford

4.98 out of 5 average rating, 697 reviews

Vermont Home Central to Ski Areas-No Cleaning Fees

Comfortable guesthouse located conveniently on US Route 7 near ski areas. Half hour from Manchester Outlet Stores. Near Long Trail/Appalachian Trail, Weston and Dorset Playhouses and miles of scenic country roads. Close to Elfin Lake and White Rocks National Recreation Area.Great for couples, small families, solo adventurers, and business travelers. Queen size bed and full kitchen. Great for overnight stay or week-long vacation to enjoy the beauty of Vermont. No cleaning fees!

4.97 out of 5 average rating, 394 reviews

Cottage in Windsor

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.

4.86 out of 5 average rating, 184 reviews

Apartment in Rutland

Baby Queens Barbie-core Studio Apt (dog friendly)

Enjoy a stylish experience at this centrally-located place. This studio apartment is perfect for the solo traveller or couple. The queen bed is super comfy. Brand new and renovated throughout. The kitchen is stocked for basic cooking. I'll make sure there is always coffee and cream for you. Pets are welcome if they do not get up on the furniture. It's easy access to downtown Rutland to enjoy yoga studios, restaurants, and coffee shops.

4.96 out of 5 average rating, 131 reviews

Dog-Friendly Mtn Escape/AC/Pool/

Experience year-round adventure at Sunrise Village at Killington, just steps from scenic trails and the Sunrise Village Triple Lift (488 ft away). After a day of outdoor fun, unwind by the cozy electric fireplace. Explore nearby hiking, mountain biking, kayaking, and golfing. The indoor sports complex—featuring a pool, hot tub, and gym—is a short walk away. Perfect for outdoor lovers looking to relax and make unforgettable memories!

4.96 out of 5 average rating, 610 reviews

Apartment in Rutland

Your home away from home

Another glorious time of year in Vermont! Our house is close to the mountains (Killington, Pico, Okemo). You'll love our space for its central location to lakes, hiking, skiing, golf, restaurants and dining, downtown, art and culture, shopping and medical facilities.This first floor apartment with its home-like atmosphere has a separate entrance. It is good for couples, small families, solo adventurers, and business travelers.

4.97 out of 5 average rating, 115 reviews

Townhouse in Killington

Beautiful Spacious Condo at Killington Resort

This cozy and spacious Sunrise Mountain Village condo is perfectly situated to nearby mountain sports at Killington Ski Resort. It welcomes up to eight guests for an unforgettable stay in the Green Mountains! Exceptional access to year round outdoor activities, great community amenities, and a comfortable condo to come home to - what more could you ask for? Book Timberline K4 today for a thrilling Vermont getaway!

4.98 out of 5 average rating, 108 reviews

Home in Killington

CozyDen - AC, Grill, Bike to Mountain!

Welcome to our cozy 1-bedroom condo in Killington, VT! Ski off and shuttle on, close to everything including biking and golfing. Enjoy the wood-burning stove, comfortable furnishings, and well-equipped kitchen. Rest well in the king bed and explore the slopes, trails, and golf courses nearby. Relax on the porch or by the fire. Your perfect Killington getaway awaits!

4.99 out of 5 average rating, 112 reviews

Cozy Condo next to Resort * AC and Pool *

Updated 1 Bdr Whiffletree condo in the heart of Killington minutes from everything. The condo is fully stocked with all of the essentials you will need for your Vermont get away. Ski locker for all your gear! King bed and Queen pullout sofa sleeps up to four (4). This property is Shuttle In/Out (Sat & Sun and holiday periods Dec - April). Killington Reg #004858

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Other great vacation rentals in Bear Mountain

5 out of 5 average rating, 8 reviews

Home in Tinmouth

Charming Vermont Schoolhouse

RobinRating, 5 stars1 day ago

My husband and I absolutely loved staying at Scott’s beautifully remodeled Schoolhouse. Scott was super responsive and very flexible for our arrival. Upon arrival the we were pleasantly surprised and greeted by a very friendly Rooster! We also loved how spotless and immaculate the entire house was. We loved the spaciousness and we felt right at home. Bed was super comfortable and Scott and his wife had thought of every possible little thing that you might need in the bathroom. We also had a welcome basket of goodies that we really enjoyed. I highly recommend that you book this place! You will not be disappointed. In fact we have already booked it for a return trip in August. We loved the large windows and decor of the home. You can tell that they put a lot of thought into making this a comfortable and relaxing space. Kitchen was also well appointed. Location was very quiet and peaceful. This place is top notch!

5 out of 5 average rating, 6 reviews

Home in Plymouth

Charming Modern Cabin Retreat

LailaRating, 5 stars2 weeks ago

My husband and I chose this home as a little getaway to celebrate my graduation. It is so peaceful and the property is beautiful. We really enjoyed how clean the home is. And how quiet it was. We truly felt comfortable and at home. I also want to highlight how responsive and nice Maribel is.

5 out of 5 average rating, 6 reviews

Apartment in Killington

Cozy Woods Resort and Spa Condo

LaraRating, 5 stars3 weeks ago

We really enjoyed our stay! The place was so clean and we felt right at home. There was plenty of space for our family and we really enjoyed having access to the indoor pool and a fireplace. Jody was responsive and helpful - a great host!

4.98 out of 5 average rating, 51 reviews

Cabin in Bridgewater

500 Acre Farm Retreat: OQ Farm's Priory

KeriRating, 5 stars1 month ago

If you are aiming to book an experience, more than just a traditional stay, do not hesitate and book now! We traveled to OQ Farm with our three daughters (my 8 year-olds request!) and it was an incredible experience being part of the farm and exploring the property. Accommodations were spacious, clean and well appointed. The hosts (and children) are approachable, kind and felt being amongst old friends! There were tears as we left. We have already recommended OQ Farm to family and friends. And our daughters are planning their return to the farm! Unforgettable!

4.95 out of 5 average rating, 22 reviews

Apartment in Killington

Cozy Killington Condo

LynetteRating, 5 stars3 weeks ago

We loved how close the hot tub and pool were to the condo.

Superhost

4.58 out of 5 average rating, 57 reviews

Snow Better Place: Perfect for 2. Hot Tub

MichaelRating, 5 stars4 months ago

Great spot for quick access to Killington’s Snowshed and Ramshead lifts. Clean and easy to get into. We were in unit E2A and the bed was a quite firm memory foam. Overall solid choice while in Killington

5 out of 5 average rating, 66 reviews

Farm stay in Clarendon

Dream Catcher Farm

Deborah JRating, 5 stars2 weeks ago

Deanna was a SuperHost as if the word was created for her. I, especially, felt at home. She's delightful, caring and sweet. Deanna's family and her dog Bella are so very welcoming. Bella should be listed as SuperHost #2! Her home is peaceful & beautiful > during the early mornings, there's multitudes of birds which made my Merlin (Bird Identifier) App go wild, including uncommon and rare birds. At night from the deck, viewing white tail deer and a BIG blue heron, and fall asleep with frog murmurs. The location perfectly afforded me several options of my intended adventures (kayaking a different lake each day.) The accommodations and its location, made my daily excursions easy to prepare for each night and leave the day to simply explore and enjoy my day. Location is everything. This was my 2nd time visiting here; and this will be one of MY places to go. CYA in July Deanna!