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Featured Condo Rentals in Bennington and around

Beautifully renovated 2 bedroom condo in Stratton VT - walk to Village/Lifts!
Exterior

Beautifully renovated 2 bedroom condo in Stratton VT - walk to Village/Lifts!

Beautifully renovated 2 bedroom condo in Stratton VT - walk to Village/Lifts!
Steps to Stratton Village, Lifts! Duplex Condo!
Property grounds

Steps to Stratton Village, Lifts! Duplex Condo!

10.0 out of 10, Exceptional, (1)
"Location was amazing and the condo was great. Clean, well-stocked. We even cooked most of our meals there. Very happy with the property and mountain. We had a blast!"
Steps to Stratton Village, Lifts! Duplex Condo!
Renovated Ski-In/Ski-Out Peru Condo at Bromley Mtn
Aerial view

Renovated Ski-In/Ski-Out Peru Condo at Bromley Mtn

9.4 out of 10, Exceptional, (28)
"My family and I had a wonderful stay for our Bromley ski week! Location couldn’t be better, and the condo was comfortable and cozy. We truly enjoyed being able to use the fireplace. Easy checkin/checkout, great communication. Being able to bring our dog was the best benefit of all - he loves the snow and spending time with us on vacation!"
Renovated Ski-In/Ski-Out Peru Condo at Bromley Mtn
5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio
Outdoor pool, a heated pool

5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio

9.6 out of 10, Exceptional, (9)
"We had a great time staying in Ashley’s condo! It was clean and well kept and super close to the village and slopes. I will definitely be back soon :)"
5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio
Lovely ski-in/out condo steps from ski lift with trails and amazing views
TV, fireplace

Lovely ski-in/out condo steps from ski lift with trails and amazing views

8.6 out of 10, Excellent, (20)
"Wonderful stay. Thanks again"
The price is €552
includes taxes & fees
12 Jan - 13 Jan 2025
Lovely ski-in/out condo steps from ski lift with trails and amazing views
Stratton Mtn Studio | Renovated | Walk to Lifts
Exterior

Stratton Mtn Studio | Renovated | Walk to Lifts

10.0 out of 10, Exceptional, (24)
"Spent one night here with family as a spontaneous ski trip, and we had a wonderful experience. Caitlin was quick to provide answers to questions prior to our arrival, and shared local recommendations. The check in process was quick and easy. The place exceeded our expectations - very clean, beautifully designed with some fun luxurious surprises. The hot tub, pool, and sauna were open, and well maintained (short indoor walk to the north building). We hope for another opportunity to stay here."
The price is €676
includes taxes & fees
9 Jan - 10 Jan 2025
Stratton Mtn Studio | Renovated | Walk to Lifts
Stratton Mountain, Nearly Ski In/Ski Out, Obertal C Building, 2 Bedrooms, 1 Bath
TV, fireplace, DVD player

Stratton Mountain, Nearly Ski In/Ski Out, Obertal C Building, 2 Bedrooms, 1 Bath

9.8 out of 10, Exceptional, (153)
"Clean and cozy condo. We had a great ski weekend. Perfect location, under a minute walk to the lift. Would definitely stay again. "
Stratton Mountain, Nearly Ski In/Ski Out, Obertal C Building, 2 Bedrooms, 1 Bath
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Terrace/patio

Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities

6.8 out of 10, (12)
"Enjoyed the amenities. Owner provided provisions like dish washing soap, laundry detergent, garbage bags which made the stay more enjoyable."
The price is €399
includes taxes & fees
7 Jan - 8 Jan 2025
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Stratton 1 Bedroom Long Trail Condo, Walk to Village and Lifts
Fridge, microwave, oven, stovetop

Stratton 1 Bedroom Long Trail Condo, Walk to Village and Lifts

9.6 out of 10, Exceptional, (45)
"Great location to mountain and village. Small room but great for a family of 4- (kids only 6 and 8). Will grow out of this space with older kids. Great proximity to pool too! Loved it."
Stratton 1 Bedroom Long Trail Condo, Walk to Village and Lifts
Top Flr Duplex 3BR 4BA - Walk to All @ Stratton Mt
Snow and ski sports

Top Flr Duplex 3BR 4BA - Walk to All @ Stratton Mt

10.0 out of 10, Exceptional, (6)
"We had the best stay in this spacious 3 BR ski chalet. Well appointed, comfortable, fully stocked kitchen, plenty of seating & great layout. Hot tub, sauna & pool were awesome at end of ski day. And the heated parking garage was really nice. It made the load/unload aspect a snap. I’d definitely stay again. Carl was a terrific host."
Top Flr Duplex 3BR 4BA - Walk to All @ Stratton Mt
Ski In/Ski Out Lofted 3BR/3Bath Stratton Mountain Village Condo
Fridge, microwave, oven, stovetop

Ski In/Ski Out Lofted 3BR/3Bath Stratton Mountain Village Condo

9.6 out of 10, Exceptional, (9)
"We traveled with 4 adults and 5 teens (one pre-teen) boys. The upstairs loft area was perfect for all the boys! There was more than enough sleeping room and the fact that they had their own bathroom was great for us adults! The boys very excited to find video game consoles. The home owners also provided a ton of board games, which we all enjoyed playing together. The space overall was great and the condo came well equipped with kitchen needs. The closets were huge and left us plenty of space...
Ski In/Ski Out Lofted 3BR/3Bath Stratton Mountain Village Condo
Mountain-view condo with private balcony, fireplace, & updated interior
Snow and ski sports

Mountain-view condo with private balcony, fireplace, & updated interior

8.2 out of 10, Very good, (11)
"A short walk to the base of Stratton, my son hiked to the peak and loved the views! It's close to other towns, and a perfectly outfitted condo with plenty of space and amenities. Dishwasher hadn't been emptied (a note for the cleaning service) but otherwise was neat and clean. Thank you!"
Mountain-view condo with private balcony, fireplace, & updated interior
Ski on ski off condo
Interior

Ski on ski off condo

10.0 out of 10, Exceptional, (62)
"We came to Stratton for the 29029 event. We have both participated before and this year we’re volunteering. We knew we wanted to stay close to the base lodge and this was the perfect location - an easy 10 minute walk. The condo was clean and we really liked having a fulll kitchen and washer/dryer. The shower was great after spending 8 hours at the summit - great water pressure and loved the rain shower head! Would definitely book again!"
Ski on ski off condo
Just steps away from Stratton Village
Fridge, microwave, oven, stovetop

Just steps away from Stratton Village

10.0 out of 10, Exceptional, (1)
"Perfect location and exactly as described. Owner was very responsive to all questions. We’d love to come back again soon!"
Just steps away from Stratton Village
Ski-In/Ski-Out Chalet on Bromley Mountain; Newly Renovated 2 bed
Outdoor pool

Ski-In/Ski-Out Chalet on Bromley Mountain; Newly Renovated 2 bed

9.8 out of 10, Exceptional, (34)
"Reasonably priced and nicely appointed condo for a couple or small family. Attractively decorated living room, easy not fussy. We enjoyed the glow from the fireplace each evening. Master bedroom mattress is memory foam and very comfortable. Close to Manchester for shopping or dining, plenty of nearby hiking trails. History buffs stop to tour The Lincoln Family Home Hildene. We aren’t skiers but you are at the top of the mountain and steps to the sky lift for easy end of day."
Ski-In/Ski-Out Chalet on Bromley Mountain; Newly Renovated 2 bed
Perfect location! Walking distance to Stratton Village and Stratton Mountain!
Exterior

Perfect location! Walking distance to Stratton Village and Stratton Mountain!

10.0 out of 10, Exceptional, (25)
"My husband and I and our 2 adult kids enjoyed our stay in this condo. It is an easy walk to the village and slopes. Great sunrise view from the living room too."
Perfect location! Walking distance to Stratton Village and Stratton Mountain!
Perfect location for your next Vermont Getaway!
Interior

Perfect location for your next Vermont Getaway!

9.2 out of 10, Wonderful, (5)
"For the most part as advertised. Checkin and checkout was easy and efficient. There was supposed to be a binder of instructions on the dining room table, we never found it but got by. Easy walk to Stratton Village, Mulligans happy hour specials were hard to beat. Kitchen supply of pots and pans was a bit sparse, if one wanted to prepare a dinner for 6, it might be challenging. Overall a good experience."
The price is €1,337
includes taxes & fees
5 Jan - 6 Jan 2025
Perfect location for your next Vermont Getaway!
Adventure Home: Trails, Pool, Gym & Tennis Access
Fireplace, DVD player, stereo

Adventure Home: Trails, Pool, Gym & Tennis Access

10.0 out of 10, Exceptional, (24)
"The place is great. Very close to Bromley and a short ride to Stratton. Easy checkin. Checkout expectations were not documented anywhere so a bit unclear there."
Adventure Home: Trails, Pool, Gym & Tennis Access
Ski on Ski off steps away from Stratton Village
Interior

Ski on Ski off steps away from Stratton Village

2.0 star property
10.0 out of 10, Exceptional, (1)
"The property was exceptionally clean and well appointed throughout! Sierra was an exceptional host being friendly, helpful and warm throughout the stay!!"
Ski on Ski off steps away from Stratton Village
Mountainside resort condo, hot tub, gas fireplace, bus to slope, wifi, w/d
Fridge, microwave, oven, stovetop

Mountainside resort condo, hot tub, gas fireplace, bus to slope, wifi, w/d

Mountainside resort condo, hot tub, gas fireplace, bus to slope, wifi, w/d
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Bennington

Perfect for Leaf Peeping w/Bar Room, Hot Tub
Interior

Perfect for Leaf Peeping w/Bar Room, Hot Tub

10.0 out of 10, Exceptional, (11)
"Wonderful experience, extremely communicative and helpful management, and just a beautiful building to stay in. We wanted for nothing. Thank you!"
Perfect for Leaf Peeping w/Bar Room, Hot Tub
Cross Country Ski? Downhill? Prospect and Mt Snow. Winter wonderland book now.
Exterior

Cross Country Ski? Downhill? Prospect and Mt Snow. Winter wonderland book now.

9.8 out of 10, Exceptional, (132)
"Linda was amazing from beginnin'g to end to ensure a comfortable stay. This house was beautiful and so cozy to stay in. The loft bed had a gorgous view of the lake and snow. Plenty of sleeping room for my kids.They got to play in the snow too:)"
Cross Country Ski? Downhill? Prospect and Mt Snow. Winter wonderland book now.
Two Brooks Lodge, Beautiful Waterfront Vermont Retreat
Fridge, microwave, oven, stovetop

Two Brooks Lodge, Beautiful Waterfront Vermont Retreat

8.8 out of 10, Excellent, (27)
"In town for a long weekend and loved the location. The owner was prompt and very helpful as we made a mistake in booking. FYI, The pictures are great but it’s a bit more rustic than they make it seem. Still, it was great to sit outside and hear the brooks flowing. Very quiet street! Housecleaning was a bit lacking though as there were some huge cobwebs in the corners. That was fine for us as we spend our time in a barn anyway. "
The price is €339
includes taxes & fees
1 Jan - 2 Jan 2025
Two Brooks Lodge, Beautiful Waterfront Vermont Retreat
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

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How can I find cheap condos in Bennington?
Expedia can help you narrow down your search for cheap condos in Bennington. To discover your perfect stay in just a few clicks, use our convenient filter tool to refine your search by star rating, amenities and budget.
What is there to do in Bennington near my condo?
Bennington has enough activities and sights to keep you going for weeks (or months!), beginning with Prospect Mountain Cross-Country Ski Centre. Woodford State Park, Prospect Mountain Nordic Ski Centre and Old First Congregational Church are other awesome attractions. If you’re in town a while, Norman Rockwell Exhibition and Robert Frost Stone House Museum will add the finishing touches to your itinerary.