
House vacation rentals in Middlesex
Find and book unique houses on Airbnb
Quick stats about house rentals in Middlesex

Total vacation rentals
Explore 70 vacation rentals in Middlesex

Nightly prices starting at
Middlesex vacation rentals start at G$12,543 GYD per night before taxes and fees

Verified guest reviews
Over 6,410 verified reviews to help you choose

Family-friendly vacation rentals
50 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
70 of Middlesex vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Middlesex rentals

4.9 Average rating
Middlesex stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated house rentals in Middlesex
Guests agree: these houses are highly rated for location, cleanliness, and more.

The 1919 Mountain Farmhouse, new hot tub and patio
Welcome to your charming mountain getaway—The 1919 Mountain Farmhouse! Located just 10 minutes away from Montpelier and 40 from Stowe proper, this newly renovated 1919 farmhouse comfortably sleeps 8 and is the perfect choice for a relaxing stay. Nestled among quiet farmland, you and your guests will enjoy sipping coffee/wine on the back deck with full mountain views. After a fun day enjoying local trails, shops, mountains, and more—a table inside or outside awaits a meal to be shared with all.

Cozy Bow House Perched in Trees w/ Hot Tub & View
The cozy Bow House is perched up above a lovely valley and boasts large south facing windows, a unique bowed loft and a warm, inviting space to relax. Up a charming dirt road past Brushwood & Fairlee Forests with hiking, biking and ATV trails nearby. Lake Fairlee is a scenic 10 min drive; 15 min to Lake Morey & I-91 and 30 min to Dartmouth College. Enjoy the glow of the rising sun and beautiful views above the fog, unwind in the hot tub surrounded by the magical woods and wildlife of Vermont.

Stunning Views near Stowe /Mountain private home
Retreat and relax at this incredibly located & uniquely designed home nestled in the heart of ski country. This three bedroom, two bathroom vacation home is perfect for families or couples looking to enjoy Vermont's beauty and recreation. Very private location minutes to the attractions of Stowe, Waterbury and Mad River Valley. Enjoy the hiking trails very close to this cozy home or the nearby ski slopes of Stowe. Sweeping views of the mountains throughout the house. Serene and lovely.

Peaceful setting with Mountain Views
Rent the entire house. Primary bdrm w/ private bath, 2 bdrms that accommodate 4 people w/ shared full bath, one bonus room w/ pull out couch and a 1/2 bath . Updated kitchen, propane stove (looks like a wood stove) covered porch, exercise room, games, fully equipped kitchen, hot tub (from Memorial Day till Thanksgiving), outdoor fire pit, all on 8 acres. Located centrally to three ski resorts, mountain biking, hiking , kayaking, swimming, you name it. An inviting home in any season!

The Spring Hill House
Escape to a haven of natural beauty and tranquility at The Spring Hill House. Our unique bow roof home offers breathtaking views of Camel’s Hump and the majestic Green Mountains, the perfect setting for a rejuvenating getaway. Despite being removed from the hustle and bustle of city life, The Spring Hill House is still centrally located, providing easy access to some of Vermont's most popular destinations. Please note: We have a firm no kids policy due to the open loft and stairs.

Home on Flower Farm near VT’s best skiing & brews!
Country setting adjacent to a flower farm only 3 minutes off 89 perfectly nestled between mountains that boast hiking, skiing and mountain biking and the best of Vermont's brewery and restaurant scene. 20 minutes to Sugarbush and Mad River Glen, 30 minutes to Stowe and 25 minutes to Bolton Valley (night skiing!). With Waitsfield and Waterbury being less than 10 minutes away, it's an easy drive to two of the finest breweries, Lawsons and Prohibition Pig, that Vermont has to offer.

Cozy home with mountain views
Welcome to our charming one-bedroom getaway, just moments away from Stowe! Experience cozy comfort with an open floor plan that makes the house feel delightfully spacious. Sholan Road presents a moderately steep and uneven incline, not suitable for low sports cars. While the driveway and Sholan Road will be cleared during the snowy winter season, it's crucial to note that effective winter tires with front-wheel, all-wheel, or 4-wheel drive are essential for safe navigation.

Secluded Mad River Valley Cabin: Chef’s Kitchen
Discover a private Vermont retreat in the heart of the Mad River Valley. Shielded in the pines, our well-appointed cabin offers a quiet escape within a scenic 25-minute drive to Sugarbush and Mad River Glen. It’s an ideal base for skiing, hiking, swimming holes or fly fishing the nearby Mad River. After a day of adventure, enjoy local dining or cook a gourmet meal in our chef’s kitchen. Perfect for those seeking both outdoor thrills and total relaxation. Follow @mrvstays

Vermont Getaway Home - Perfect Location
Central Location! Covered patio with propane fire table. Cozy 2 bed, 1.5 bath home, in a 2 unit duplex, 1200 sq.ft. Fully furnished. Whether you choose to stay in or want to get out, this is a great location! 13 mi. to Stowe Mtn., 21 to Sugarbush, 25 to Burlington, 3 to local hiking trails, and 4 to downtown Waterbury, enjoy local restaurants, craft beer, and more! Bedrooms and full bath are on 2nd floor. AC throughout the house! Smoke Free, Pet Free Rental.

Spacious Eco-Friendly Stowe Home for Family Fun
Vacation/Work Remotely or both in this 5 BR and 5 BA gorgeous mountain eco-friendly home. FIBER 100 meg symmetrical wifi, a quiet workspace with desk, monitor, and printer. Fully stocked kitchen, ping pong, fire pit, large family space but quiet spaces too, and 3 ensuite bedrooms! Conveniently located close to town and a short drive to skiing. This is a great family space to reconnect or a space to work remotely for a change of pace.

Cozy Hideaway w Hot Tub — Bike, Hike, Play & Relax
Welcome to our lovely 1865 Waterbury Village Hideaway. We are located 1/2 mile from the very best Mountain Biking trails, less than 1 mile to great food and beer, access to more than 7 Ski Resorts, including Stowe, Sugarbush & Killington, and 30 minutes from Burlington and the Waterfront. Use this Hideaway to take advantage of everything Vermont has to offer and relax in the soothing waters of our Hot Tub at the end of the day.

Restored 1840s Farmhouse Between Stowe & Waterbury
Restored 1840s Vermont farmhouse ideally located between Stowe and Waterbury. Spend your days skiing, hiking, biking, exploring local breweries and restaurants, or enjoying Vermont's lakes and trails, then come home to a warm, welcoming space full of character. With exposed beams, wide plank floors, radiant heat, a spacious yard, and room for up to 8 guests, the farmhouse combines historic charm with the comforts of modern living.
Popular amenities for Middlesex house rentals
House rentals with a pool

Mountain View Farmhouse w/ Orchard, Pool is Open!

EPIC Stowe Getaway - Great For Families & Friends

Charming Barre Getaway

Serene Mountain Studio Spruce Peak Lodge | 1328

SugarBear- Pool, AC, Sauna, Gym, Tennis!

Lakefront Peaceful Getaway in Mountain Lakes

Luxury Condo Tucked in the Heart of Killington

Charming Sugarbush Standalone Condo
Weekly house rentals

Mountain Oasis/10 Mins to Stowe/Hiking/HotTub

4CR Farm Guest House 4 Season Vacation Destination

Vermont Cedar Cottage | Fireplace & Pond Views

Modern Farmhouse on 25 Acres - Superb Views

Cozy Mountain Home w/Million $ View

Modern Barn Perched on 24 Acres w/ Stunning Views

Mountainside Lodge, near wedding barns/Stowe

Panoramic Mountain Views. Quiet, Private & Clean.
Private house rentals

Architectural House Prickly Mountain

Convenient Retreat

Year-round mountain escape, stunning views!

Best Reviews~Perfect VT Modern Style~View Hot Tub

Modern Design Retreat: Sauna + Views Near Stowe

Perry Pond House

Recreation Paradise on 600+ Acres

Sky Zen - Ridgeline Retreat
When is the best time to visit Middlesex?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$53,307 GYD | G$61,041 GYD | G$46,826 GYD | G$41,809 GYD | G$47,662 GYD | G$42,227 GYD | G$47,035 GYD | G$43,063 GYD | G$45,154 GYD | G$47,453 GYD | G$41,809 GYD | G$49,962 GYD |
| Avg. temp | -6°C | -5°C | 0°C | 8°C | 15°C | 20°C | 22°C | 21°C | 17°C | 10°C | 4°C | -2°C |
Destinations to explore
- New York Vacation rentals
- Montreal Vacation rentals
- Boston Vacation rentals
- Quebec City Vacation rentals
- Portland Vacation rentals
- Jersey City Vacation rentals
- Newark Vacation rentals
- Mont-Tremblant Vacation rentals
- Newport Vacation rentals
- Providence Vacation rentals
- Bar Harbor Vacation rentals
- Salem Vacation rentals
- Jay Peak Resort
- Sugarbush Resort
- Pico Mountain Ski Resort
- Dartmouth College
- Bolton Valley Resort
- Jay Peak
- Stowe Mountain Resort
- Fort Ticonderoga
- University of Vermont
- Middlebury College
- Killington Resort
- Cannon Mountain Ski Resort
- Jay Peak Resort Golf Course
- Kingdom Trails
- Montshire Museum of Science
- ECHO, Leahy Center for Lake Champlain
- Snow Farm Vineyard & Winery
- Shelburne Museum
- Warren Falls
- Shelburne Vineyard
- Pump House Indoor Waterpark
- Cold Hollow Cider Mill
- Quechee Gorge
- Fairbanks Museum & Planetarium





