Search Vacation Homes in Middlesex

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 606 Vacation Homes in Middlesex with updated reviews, rates, and availability.

Scenic country retreat with mountain views, deck, firepit, & washer/dryer

9.2 out of 10, Wonderful, (44)
"beautiful house in the woods and close to lake. really enjoyed our stay"
Scenic country retreat with mountain views, deck, firepit, & washer/dryer

Dog-friendly home with panoramic mountain views, grill, deck, & pool table

9.0 out of 10, Wonderful, (11)
"This was our first weekend stay in Vermont and it was great! I could definitely see us staying here again."
Dog-friendly home with panoramic mountain views, grill, deck, & pool table

Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you

2.0 star property
10.0 out of 10, Exceptional, (7)
"Absolutely the best hosts! Easy to work with. Quick responses to questions. Very accommodating. Beautiful setting. Perfect getaway. The goats were great barn-mates! Outdoor fire pit was perfect! Highly recommend!"
The price is AED 441
AED 576 total
includes taxes & fees
2 Jun - 3 Jun
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you

Lakefront Vacation Home on Lake Elmore

9.6 out of 10, Exceptional, (98)
"We loved the house. Would stay again. "
Lakefront Vacation Home on Lake Elmore

Huge deck, hot tub, foosball, surrounded by nature

10.0 out of 10, Exceptional, (35)
"Clean, well stocked, conveniently located "
Huge deck, hot tub, foosball, surrounded by nature

Heated pool, sauna, surrounded by nature!

10.0 out of 10, Exceptional, (20)
"House was top notch quality - grounds were beautiful, well maintained and in a quiet/secluded location! Thoroughly enjoyed our stay!!"
Heated pool, sauna, surrounded by nature!

Iron Gate Chalet - 5 Minutes to Smugglers Notch and Wedding Barn!

10.0 out of 10, Exceptional, (38)
"The stay was exactly as described. Great location on the mountain near lots to do. The dog loved the room to run around outside. The interior has great cozy ski house vibes which was perfect for our winter get away. Would highly recommend staying here and would love to return again in the future. "
The price is AED 771
AED 1,724 total
includes taxes & fees
10 Jun - 11 Jun
Iron Gate Chalet - 5 Minutes to Smugglers Notch and Wedding Barn!

Stowe Toll House Double Lift Ski in/out Gem

10.0 out of 10, Exceptional, (3)
"Beautiful place, perfect location to ski out/in"
Stowe Toll House Double Lift Ski in/out Gem

Escape 2 Stowe: 5 minutes from village of Stowe

9.8 out of 10, Exceptional, (42)
"The property was all that was advertised. Beautiful view from the back deck. All amenities were great! Thank you!"
Escape 2 Stowe: 5 minutes from village of Stowe

New! Vermont modern farmhouse in Stowe Village

10.0 out of 10, Exceptional, (74)
"We all really enjoyed our stay here. The location is very convenient to town. We walked into town for dinner most nights, but cooking meals at home was no problem either. The weather was frigid while we were there but the house was warm and cozy. There is an open plan kitchen with everything you need for cooking. We highly recommend staying here!"
New! Vermont modern farmhouse in Stowe Village

Stowe Retreat (Mountain Views & Fenced Backyard) by RedAwning

2.0 star property
10.0 out of 10, Exceptional, (1)
Stowe Retreat (Mountain Views & Fenced Backyard) by RedAwning

Great location, sleeps 10 , close to mountain/town , hot tub, 3 full baths

9.6 out of 10, Exceptional, (237)
"Unfortunate rodent problem, but otherwise a great place with all the amenities you could want on a ski break. Owner is in the process of fixing."
Great location, sleeps 10 , close to mountain/town , hot tub, 3 full baths

Off Grid Glamping Shed with River Access

2.0 star property
The price is AED 239
AED 370 total
includes taxes & fees
2 Jun - 3 Jun
Off Grid Glamping Shed with River Access

Stowe Riverfront Townhome...... The Perfect Summer Retreat

10.0 out of 10, Exceptional, (67)
"Chas and Jeanette's condo was perfect for our ski weekend. The location couldn't be better, walkable to a grocery store, restaurants, and shops in beautiful downtown Stowe. The fireplace was a nice perk and the views of the river out back were very nice. Beds were comfortable!"
Stowe Riverfront Townhome...... The Perfect Summer Retreat

Come join us for summer fun on the mountain!

9.0 out of 10, Wonderful, (19)
"Condo is nice and comfortable for our family - lovely family room, fireplace and view of the mountains. Ski out when Timberline lifts open, otherwise right next to the mountain, secluded away from crowds of the resort so best of both worlds. Family enjoyed our stay and really liked Bolton Valkey ski area. "
Come join us for summer fun on the mountain!

Large, Comfortable, Retro 1970s Hillside Chalet

8.8 out of 10, Excellent, (47)
"Great place in a great area. "
Large, Comfortable, Retro 1970s Hillside Chalet

Gas woodstove, central location!

2.0 star property
9.6 out of 10, Exceptional, (4)
"My family and I stayed here and absolutely loved it. Peaceful and quiet enough to completely disconnect, but close enough to the town and mountain to have everything you could need. We especially enjoyed the small market up the street (Cork market). "
Gas woodstove, central location!

Stowe Escape: Hot Tub, Hikes & Mountain Vibes!

The price is AED 694
AED 1,835 total
includes taxes & fees
2 Jun - 3 Jun
Stowe Escape: Hot Tub, Hikes & Mountain Vibes!

Just Renovated-Spacious Home ideally located in the middle of Stowe

9.8 out of 10, Exceptional, (31)
"We had an excellent ladies trip to Stowe. It even snowed! Your home met all our needs and was beautiful."
Just Renovated-Spacious Home ideally located in the middle of Stowe

Vermont charm, close to Village!

10.0 out of 10, Exceptional, (5)
"Very cool - updated historic house!"
Vermont charm, close to Village!
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.
Save an average of 15% on thousands of hotels when you're signed in