
Holiday houses in Middlesex
Find and book unique accommodation on Airbnb
Quick stats about holiday rentals in Middlesex

Total holiday rentals
Explore 140 holiday rentals in Middlesex

Nightly prices starting at
Middlesex holiday rentals start at $68 NZD per night before taxes and fees

Verified guest reviews
Over 14,400 verified reviews to help you choose

Family-friendly holiday rentals
70 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wi-Fi availability
130 of Middlesex holiday 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 holiday rentals in Middlesex
Guests agree: these stays are highly rated for location, cleanliness and more.

Jules Gem
Reconditioned Barn Apartment. One large room with 4 large windows creating much natural light with kitchenette, no oven at this time, but there is a toaster oven & BBQ Grill for your use Overlooking Mountains and situated next to a river. Enjoy the sounds and views of country on this 90 acre property. All new amenities and full bath with shower. Private swimming hole on property, steps from sought after hiking, 12 minutes to downtown Montpelier with fine dining, bars and unique shopping.
ValueLocationLong stay

Secluded Luxury Treehouse - Hot Tub + Projector
Our treehouse is a haven of well-being, peace, and elegance. In our stunning modern treehouse we have brought relaxation to a whole new level. Surrounded amongst us is nothing but woods & wildlife. An experience not to be missed. Put your favorite movie on the projector, get Zen in the cozy sun room, jam out to music on the record player, or grab a towel, and head for the custom cedar hot tub. It is time to create core memories that will never be forgotten. Welcome to a little slice of heaven.
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Cady’s Falls Cabin
Welcome to our treehouse inspired, modern cabin overlooking The Kenfield Brook on Terrill Gorge. We are located 5 miles from Stowe and its attractions, and just a few minutes from downtown Morrrisville with all its amenities. Just upstream from the picturesque Cady’s Fall swimming hole and across the brook from the amazing Cady’s Falls bike trails, our cabin is perched atop the hillside. With its simple, minimalist design it’s easy to immerse yourselves in nature and feel at home in the trees.
LocationValueIndoor spaces

Cozy Studio/Romantic Getaway
Take it easy at this cozy studio which is nestled in the hills of the beautiful Duxbury Vermont. Offered year round so that our guests can enjoy all that Vermont has to offer such as nearby skiing, changing leaves, hiking and so much more! Guests will enjoy their own private space with access to many amenities such as a full kitchen, private entrance, a queen bed, free WIFI and so much more! So grab a mug and sit back and relax next to the gas fireplace! You will want to return every season!
ValueLocationCleanliness

Weasley's Enchanted Treehouse @ Vermont ReTREEt
Welcome to our enchanting treehouse! We crafted this unique and magic inspired dwelling for any admirer of a beloved wizarding world, or anyone who appreciates isolation in a fun space. As you cross the elevated walkways, you'll feel like you're entering a wizards treehome in the forest. The 1,100 sqft treehouse is nestled in and among trees, providing a magical and secluded escape from life. Have a question or hesitations? reach out check out our other listings for glamping style treehouses
FamilyValueQuiet

The Summit House - remodeled unique A-frame
Welcome to The Summit House, a completely renovated A-Frame cabin less than 1 mile to downtown Stowe. Wake up to views of the morning light casting through the forest from your glass wall bedroom. Relax after a day exploring the mountains in the huge spa style rainfall shower. Settle down after dinner around the modern wood burning fireplace while watching your favorite shows on the 50" TV. It's not just a rental, it's an experience. The latest addition to the OM Home Residences collection.
LocationValueIndoor spaces

Stunning timber frame home on Cady Hill
Wrap yourself in the warmth of our recently finished, one-of-a-kind timber frame straw bale home - aka DD's House. Owner-built in honor of our beloved Grandma DD, we welcome you and yours to enjoy some trailside quality time together as you relax after a day of skiing, hiking, mountain biking, or simply enjoying the beauty of Stowe, Vermont. Located right next to Stowe's Cady Hill Forest, this thoughtful design will present you with truly unique construction and finish details.
LocationOutdoor spacesQuiet

Farmhouse with Sunset Mountain Views
Unbeatable Vermont setting, panoramic mountain views and gorgeous sunsets. Located one mile off Rt 100, minutes from the best skiing, bike trails, kayaking, and hiking in the east. The apartment is a sunny, bright and private space, cheerfully decorated, with the comfiest beds and coziest linens. And great outdoor spaces to relax in at the end of the day! 10 min to Stowe Village, 18 to lifts, 30 to Sugarbush, 35 min Burlington. The pictures and our 5 star reviews say it all!
FamilyLocationComfort

Morningstar Meadow - your home in Vermont
You have a home in Vermont! 5-star one-bedroom apartment has country charm and contemporary panache. A perfect retreat to enjoy rural serenity, stunning views, woods and fields. Everything you need: well-appointed with attractive, high quality furnishings, separate entrance, full kitchen, open living/dining area, cozy bedroom with queen bed. Cable TV, WiFi, and cell service. Plentiful free parking. Recent guests claimed heat an issue. It is not. No complaints before or since.
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The Roost - Recharge & Relax
Enjoy being immersed in nature when you stay in this unique treehouse to unwind while experiencing some of the best sights and nature in Vermont. This cabin up on stilts and bordering one of Vermont's beautiful state parks. Views of the walkable Waterbury reservoir can be seen from its perch in the trees. "The Roost" aims for a balance of rustic meets elegance. With a tiled shower and heated flooring through out- one can truly reconnect and recharge in this unique experience.
ValueLocationDecor

Luxury Glass Tiny House - Mountain View + Hot Tub
Immerse yourself in nature at Vermont's most unique Airbnb, located in the heart of the Green Mountains. This upscale mirrored glass house was built in Estonia and combines Scandinavian design with jaw-dropping Vermont views for an unforgettable experience. You'll return home feeling rejuvenated after relaxing in a hot tub overlooking Sugarbush Mountain or waking up with a panorama of Blueberry Lake at your feet. *One of Airbnb’s Most Wish-listed Stays of 2023*
LocationValueCheckout

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.
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Popular amenities for Middlesex holiday rentals
Other great holiday rentals in Middlesex

Home on Flower Farm near VT’s best skiing & brews!
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von Trapp Farmstead Little House
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Off Grid Secluded Farm Stay Cabin
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Secluded Mad River Valley Cabin: Chef’s Kitchen
FamilyLocationAir conditioning

Charming log cabin w/ fireplace in Stowe village
FamilyValueAmenities

Pet Friendly Cozy Treetop Cabin near Mt Worcester
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A true Vermont get-away cabin in the woods
FamilyLocationWalkability

VT Glamping in our Tiny Hide-A-Way
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When is the best time to visit Middlesex?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $282 NZD | $289 NZD | $260 NZD | $245 NZD | $263 NZD | $263 NZD | $262 NZD | $238 NZD | $263 NZD | $272 NZD | $228 NZD | $272 NZD |
| 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 |
Frequently Asked Questions
Are there family-friendly vacation rentals in Middlesex?
Middlesex has more than 70 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in Middlesex?
Experience the best of Middlesex with our house rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Middlesex?
Four-legged friends are welcome in Middlesex. Choose from more than 30 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Middlesex?
Yes! Work meets play with ease at over 60 vacation rentals in Middlesex featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Middlesex have air conditioning?
Absolutely! We offer over 40 house rentals with air conditioning in Middlesex. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Middlesex have a kitchen?
Absolutely! We offer over 70 house rentals with a kitchen in Middlesex. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Middlesex have wifi?
Absolutely! We offer over 70 house rentals with wifi in Middlesex. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Middlesex have free parking?
Absolutely! We offer over 70 house rentals with free parking in Middlesex. Enjoy a tailored experience with all the comforts you desire.
Destinations to explore
- New York City Holiday rentals
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- Newark Holiday rentals
- Mont-Tremblant Holiday rentals
- Newport Holiday rentals
- Providence Holiday rentals
- Bar Harbor Holiday rentals
- Salem Holiday 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
- Jay Peak Resort Golf Course
- Montshire Museum of Science
- Kingdom Trails
- Snow Farm Vineyard & Winery
- Pump House Indoor Waterpark
- Warren Falls
- Shelburne Museum
- Shelburne Vineyard
- Cold Hollow Cider Mill
- Quechee Gorge
- Fairbanks Museum & Planetarium
- Elmore State Park
- Waterfront Park





