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Explore Similar Houses Within 25 Miles of Middletown Springs, VT

  • /59

    $4,500 per month

    • 3 Beds
    • 4 Baths
    • 2,308 Sq Ft
    • House for Rent

    1728 Vermont 30, Dorset, VT 05251

    Escape to Cody Cottage, a charming 3 bed, 3 bath home perfect for outdoor enthusiasts and families alike! Nestled next to the scenic Dorset Quarry, this cozy retreat offers easy summer swimming and breathtaking mountain views. Vaulted ceiling in the living room with dining that opens to the updated kitchen with 2 seat island. 1st Floor has the primary bedroom with en suite bath, a guest bedroom

    Agent Photo

    Laura Beckwith

    Josiah Allen Real Estate, Inc.

    (802) 694-4997

    1728 Vermont 30, Dorset, VT 05251
  • /52

    $5,000 per month

    • 3 Beds
    • 2 Baths
    • 1,932 Sq Ft
    • House for Rent

    397 Powderhorn Rd, Manchester Center, VT 05255

    Charming newly renovated ranch with 3 bedrooms, 2 baths is the perfect summer rental, offering a cozy and inviting atmosphere! Conveniently located close to town for easy access to shops and dining. Enjoy a fenced-in backyard with a deck, perfect for grilling and outdoor relaxation. The kitchen and living room are located on the first floor, along with the spacious primary bedroom featuring an en

    Agent Photo

    Laura Beckwith

    Josiah Allen Real Estate, Inc.

    (802) 729-7527

    397 Powderhorn Rd, Manchester Center, VT 05255
  • /31

    $6,500 per month

    • 4 Beds
    • 3.5 Baths
    • 2,340 Sq Ft
    • House for Rent

    294 Green Peak Orchard S, Dorset, VT 05253

    Escape to a stunning summer/winter retreat in Southern Vermont, featuring 4 spacious bedrooms and 3.5 baths. Nestled in the heart of nature, this property offers breathtaking mountain views, perfect for relaxation and outdoor adventures. Open-concept living/kitchen area with plenty of seating, a wood burning fireplace, and panoramic mountain views. Kitchen is fully equipped with modern

    Agent Photo

    Laura Beckwith

    Josiah Allen Real Estate, Inc.

    (802) 644-7034

    294 Green Peak Orchard S, Dorset, VT 05253
  • /18

    $4,500 per month

    • 4 Beds
    • 3 Baths
    • 2,500 Sq Ft
    • House for Rent

    191 Forest Mountain Rd, Peru, VT 05152

    WELCOME TO PERU MOUNTAIN LODGE... Now Available For Your Vermont Summer '25 Vacation! Don't Let This One Get away... Cozy open living area with four Bedrooms. Two bedrooms on the main level, the Main Suite in the loft above, and a fourth bedroom in the finished walk-out basement. This home boasts a cathedral ceiling, an updated cooks kitchen, and a striking stone fireplace with two

    Agent Photo

    Kristin Comeau

    TPW Real Estate

    (802) 889-8948

    191 Forest Mountain Rd, Peru, VT 05152
  • /37

    $9,000 per month

    • 3 Beds
    • 3 Baths
    • 1,980 Sq Ft
    • House for Rent

    3093 Route 30, Dorset, VT 05251

    Wonderful Dorset Village Historic Colonial, private and completely protected by the established vintage tree line that buffers the neighbors and Route 30. Walk to Village location, this property has been fully renovated with updated kitchen and baths. The house is warm and welcoming with front and side covered porch entrance while the rear screened porch creates an expansive summer room to the

    Agent Photo

    Laura Beckwith

    Josiah Allen Real Estate, Inc.

    (802) 520-2909

    3093 Route 30, Dorset, VT 05251
  • /40

    $11,300 per month

    • 5 Beds
    • 3 Baths
    • 2,472 Sq Ft
    • House for Rent

    303 W View Estates, Manchester, VT 05255

    Gorgeous 4,432 Square Foot - 5 bedroom, 3 bath Log Home in the Heart of Manchester and the Green Mountains! You won't find a better equipped, more spacious and luxury home, located in one of the best Winter and Summer vacation spots in Vermont. 1st Floor boasts a beautiful great room with cathedral ceiling, stone fireplace seamlessly flows into an open-concept kitchen/dining area. Great for

    Agent Photo

    Laura Beckwith

    Josiah Allen Real Estate, Inc.

    (802) 300-4671

    303 W View Estates, Manchester, VT 05255
  • /25

    $3,200 per month

    • 4 Beds
    • 2 Baths
    • 1,950 Sq Ft
    • House for Rent

    78 Franklin Rd, Manchester, VT 05255

    AVAILABLE NOW! WINTER RENTAL: '25/'26 As the seasons change, this charming older home in the heart of Manchester Village is ready to welcome you. With its unique traditional elements, this fully furnished home is a perfect retreat for the Winter Season.Bon appetit! Located just a couple of blocks from Manchester's Restaurant Row...Available November 15th '25, through

    Agent Photo

    Kristin Comeau

    TPW Real Estate

    (802) 300-3752

    78 Franklin Rd, Manchester, VT 05255
  • /40

    $13,000 per month

    • 5 Beds
    • 4.5 Baths
    • 4,100 Sq Ft
    • House for Rent

    21 Valley View Rd, Winhall, VT 05255

    Spectacular 5 bedroom, 5 bathroom house with panoramic mountain views!!! Entry level offers a 2 car garage, laundry room, powder room and large eat in kitchen. Beautiful views out the back sun room! Kitchen opens up to cathedral ceilings in the great room with center stone fireplace, formal dining room, foyer and den. Expansive primary suite on the first floor over looking the back deck with hot

    Agent Photo

    Laura Beckwith

    Josiah Allen Real Estate, Inc.

    (802) 328-9426

    21 Valley View Rd, Winhall, VT 05255
  • /60

    $9,000 per month

    • 4 Beds
    • 2.5 Baths
    • 3,746 Sq Ft
    • House for Rent

    81 Pine Tree Ln, Manchester Center, VT 05255

    Welcome to this stunning newly built modern farmhouse, nestled on 3 private acres in a prime location just minutes from both Manchester and Dorset. This spacious 4 bedroom, 2.5 bath home offers a perfect blend of modern comfort and farmhouse charm. Bright and airy open concept first floor with kitchen, dining area, living room, and den – all opening to a spacious patio, perfect for entertaining.

    Agent Photo

    Laura Beckwith

    Josiah Allen Real Estate, Inc.

    (802) 577-2443

    81 Pine Tree Ln, Manchester Center, VT 05255
  • /35

    $3,500 per month

    • 3 Beds
    • 3 Baths
    • 1,312 Sq Ft
    • House for Rent

    3 Bromley Forest Rd, Winhall, VT 05340

    Adorable 3 bed, 3 bath ranch located on desirable Bromley Forest Road in Winhall, just over the border from Manchester. This fully furnished home offers a perfect blend of comfort and convenience in a peaceful, wooded setting. The main level features an open and inviting layout, including a spacious living room, a fully equipped kitchen, and a cozy dining area. The 1st floor primary bedroom

    Agent Photo

    Laura Beckwith

    Josiah Allen Real Estate, Inc.

    (802) 300-3940

    3 Bromley Forest Rd, Winhall, VT 05340
  • /29

    $3,000 per month

    • 3 Beds
    • 2 Baths
    • 2,256 Sq Ft
    • House for Rent

    79 Mountain View Ave, Proctorsville, VT 05153

    79 Mountain View Ave, Proctorsville, VT 05153
  • /18

    $25,000 per month

    • 3 Beds
    • 2 Baths
    • 1,423 Sq Ft
    • House for Rent

    378 Tuttle Hill Rd, Londonderry, VT 05155

    Welcome to your turn-key home for the '25-'26 ski season! Fully renovated with attention to detail, this cheerful, sunny Scandinavian Modern space welcomes and inspires. 15 minutes to Stratton Base, 14 minutes to Bromley Village, and 10 minutes to Magic Mountain, you are in the middle of it all, with your choice to either explore or stick to your home mountain. The main floor includes a

    Jamie Luke TPW Real Estate

    378 Tuttle Hill Rd, Londonderry, VT 05155
  • /19

    $1,800 per month

    • 1 Bed
    • 1 Bath
    • 600 Sq Ft
    • House for Rent

    18 Jay Rd E, Lake George, NY 12845

    Well kept cottage - minimum rental is 30 days - available November 8th, 2025 to April 30th - fully furnished - all utilities included (WIFI, heat, water, electric, gas, snow removal) - nice view of Glen Lake (no access to the lake from the cottage) - close to Lake George Winter Carnival in February - kayak launch area 1/2 mile away on Glen Lake - 10 minutes to Lake George beach & village (resort

    18 Jay Rd E, Lake George, NY 12845
  • /19

    $65,000 per month

    • 4 Beds
    • 4 Baths
    • 2,000 Sq Ft
    • House for Rent

    16 Winterberry Heights, Stratton, VT 05360

    Best of the Best. Ski on Ski off. never rented before, pristine clean and original owners. Largest Treetops there is.. 4 bedroom/4 bath, den family room, amazing views, hot tub.. everything you want and need for an amazing winter season. Loads of room for family and guests and entertaining. Enjoy all that Stratton has to offer as well as all the other ski areas close by and Manchester shopping

    Wilkie Bushby TPW Real Estate

    16 Winterberry Heights, Stratton, VT 05360
  • /35

    $3,200 per month

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • House for Rent

    663 Depot St, Chester, VT 05143

    This newly renovated 3-bedroom, 2-bathroom property in Chester, VT offers 1,400 square feet of living space simultaneously marrying modern day convenience and open concept living with the Victorian Farmhouse feel, paying homage to the house's heritage. The living room features ample natural light and is designed for comfortable gatherings with a large screen TV equipped with Roku for you to

    663 Depot St, Chester, VT 05143
  • /35

    $9,000 per month

    • 4 Beds
    • 3.5 Baths
    • 2,908 Sq Ft
    • House for Rent

    43 Cranberry Hill Rd, Winhall, VT 05340

    First time available for a seasonal rental.Call 43 Strattonwald home for your 25-26 ski season. This recently updated modern, yet classic chalet has room for all. With four bedrooms, two of the primary bedrooms with en-suite bathrooms, there is ample room for everyone's comfort. The home has brand new bathrooms, modern decor and state of the art appliances. With several living areas

    Peggy O'neill Cummings & Co

    43 Cranberry Hill Rd, Winhall, VT 05340
  • /13

    $2,300 per month

    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft
    • House for Rent

    8 Meadow Ln, Glens Falls, NY 12804

    Charming & Spacious Queensbury Home for Rent! Welcome to Queensbury! This beautifully maintained 3-bedroom, 2-bathroom single-family home offers 1,800 sq. ft. of clean, comfortable living space — including a dedicated home office and a versatile bonus room perfect for a family or playroom. Nestled in a quiet, family-friendly neighborhood within the highly regarded Queensbury School District,

    8 Meadow Ln, Glens Falls, NY 12804
  • /65

    $4,000 per month

    • 3 Beds
    • 3.5 Baths
    • 2,268 Sq Ft
    • House for Rent

    22 Kendrick Hill Rd, Saratoga Springs, NY 12866

    Welcome to the lush, private Louden Ridge neighborhood. This award-winning showcase home blends luxury and comfort with an Adirondack-inspired contemporary design. Custom-crafted for green living by Frank Laskey with Phinney Design finishes. Meticulously maintained. First-floor primary suite with spa-like bath and soaking tub. Cozy screened porch overlooks serene fish pond. Chef's kitchen with

    Tamara Valentine Roohan Realty

    22 Kendrick Hill Rd, Saratoga Springs, NY 12866
  • /24

    $3,850 per month

    • 4 Beds
    • 3.5 Baths
    • 2,225 Sq Ft
    • House for Rent

    1802 Vt 100a, Plymouth, VT 05056

    This property at 1802 VT 100A features 4 bedrooms and 3.5 bathrooms, offering a total of 2,225 square feet of living space. An additional room could be converted to a fifth bedroom. This charming home is available for long-term lease starting Sept. 1 (or possibly earlier) and offers a perfect blend of rustic character and modern comfort. The great room provides ample space for relaxation and

    1802 Vt 100a, Plymouth, VT 05056
  • /43

    $2,650 per month

    • 4 Beds
    • 3 Baths
    • 2,532 Sq Ft
    • House for Rent

    11208 State Route 22, Fort Ann, NY 12827

    Charming farmhouse meets modern comfort! This 4-bed, 3-bath home sits on 1.1 acres and features an open-concept updated kitchen featuring granite countertops, an oversized 9' island, SS appliances, and soft-close cabinets. Enjoy the 3-season cedar room, and stylish touches like barn doors, ornate molding, and LVP flooring. The primary suite offers an updated primary bath, with a walk-in tile

    Robert Saumell Jr. KW Platform

    11208 State Route 22, Fort Ann, NY 12827
  • /14

    $17,500 per month

    • 4 Beds
    • 2 Baths
    • 1,550 Sq Ft
    • House for Rent

    4591 Vermont 30, Jamaica, VT 05343

    This is a delightful Winter retreat...After a long fun day of skiing come home to this warm and cozy, meticulously maintained 4 bedroom home that is in great shape. Just 8 minutes from Stratton access Rd.Upstairs there are 2.5 bedrooms , kitchen, and living room with wood burning fireplace. Downstairs is another full bedroom and a 2nd kitchen, full bath, laundry and family room with TV,

    Wilkie Bushby TPW Real Estate

    4591 Vermont 30, Jamaica, VT 05343
  • /16

    $35,000 per month

    • 4 Beds
    • 2.5 Baths
    • 1,800 Sq Ft
    • House for Rent

    Lot 2 89 Jaquith Rd, Landgrove, VT 05148

    This one-of-a-kind experience on a gentleman's farm in one of the beautiful locations of Southern Vermont could be yours for this upcoming ski season. Centrally located to Stratton, Okemo, Magic and Bromley.With four large bedrooms, there is room for 12 people. There are two full baths leaving no room for time constraints when everyone is trying to get out the door to hit the slopes. A

    Peggy O'neill Cummings & Co

    Lot 2 89 Jaquith Rd, Landgrove, VT 05148
  • /39

    $65,000 per month

    • 7 Beds
    • 7 Baths
    • 6,600 Sq Ft
    • House for Rent

    89 Jaquith Rd, Londonderry, VT 05148

    It's time to start planning a Vermont winter retreat like no other. This stunning, architect designed property is located centrally to Okemo, Stratton, Bromley and Magic Mountains. The property is perfect for snowshoeing, cross country skiing ice skating and apres ski warming around the rustic fire pit area. Inside, you will have breathtaking views, top of the line amenities and features abound.

    Peggy O'neill Cummings & Co

    89 Jaquith Rd, Londonderry, VT 05148
  • /24

    $10,000 per month

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • House for Rent

    29 Sunrise Ln, Bolton Landing, NY 12814

    The ultimate rental opportunity!! This Bolton Landing home has the most amazing panoramic views of Lake George, The Sagamore Hotel, and Dome Island. This 3/2 home is fully furnished .Five minutes to Bolton Landing Village. Enjoy the beach, marinas, some great restaurants and quaint shops. Less than 30 minutes to Gore Mt. Experience the 'Queen of the Adirondacks and all its glory. This prime

    Cindy Anthis Hunt ERA

    29 Sunrise Ln, Bolton Landing, NY 12814
  • /26

    $40,000 per month

    • 6 Beds
    • 3.5 Baths
    • 3,557 Sq Ft
    • House for Rent

    55 Wallis View Ln, Ludlow, VT 05149

    Winter Seasonal Rental available November 1, 2025 through April 15, 2026. Price is $40,000 plus $7000 for utility deposit and $5000 security deposit. All funds due prior to rental start. Beautiful views from this large cape-style home. Open kitchen to living room with stone fireplace. Comfortable, warm and spacious. Fully-equipped kitchen for the chef. All linens provided. Hot tub. Bed

    Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

    55 Wallis View Ln, Ludlow, VT 05149
  • /22

    $30,000 per month

    • 4 Beds
    • 2.5 Baths
    • 3,154 Sq Ft
    • House for Rent

    157 Old Sawmill Rd, Londonderry, VT 05148

    Wonderful Norwegian style chalet available for seasonal rental in southern VT ski country. Watch the snow cats on Magic Mountain from the home. Magic Mountain is 1.5 miles/4 minutes from the home. Stratton and Bromley Mountains are 20 minutes away. Okemo is 25 minutes away, and Killington is 55 minutes away. The VAST system for snowmobiling is accessible from the house, no need to trailer

    Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    157 Old Sawmill Rd, Londonderry, VT 05148
  • /19

    $3,750 per month

    • 4 Beds
    • 2 Baths
    • 2,690 Sq Ft
    • House for Rent

    282 Highland Ave, Manchester Center, VT 05255

    In town, four bedroom, two bathroom house for rent. Main floor is a large mudroom and laundry room, kitchen, dining, office, living room, and full bathroom. Upstairs is 4 bedrooms, full bathroom, storage room. Central air conditioning. Wood floors throughout. Unfinished clean basement. Wrap around covered porch. Level yard, paved driveway. Walk to town. One car detached garage. Stand by backup

    Christiane Carroccio TPW Real Estate

    282 Highland Ave, Manchester Center, VT 05255
  • /16

    $1,500 per month

    • 1 Bath
    • 936 Sq Ft
    • House for Rent

    1 Parker Ave, Ludlow, VT 05149

    Looking for a distinctive office setting with personality and practicality? This beautifully maintained 1900s building offers a professional space unlike any other. Featuring elegant marble accents, rich woodwork, and high ceilings, it blends vintage charm with everyday functionality. Plenty of built-in storage and multiple flexible-use rooms make it ideal for small businesses, creative

    Frank Provance Diamond Realty

    1 Parker Ave, Ludlow, VT 05149
  • /26

    $30,000 per month

    • 4 Beds
    • 3.5 Baths
    • 3,800 Sq Ft
    • House for Rent

    197 Monadnock View Ln, Jamaica, VT 05343

    Perfect private location only minutes to Ski resorts.Home could accommodate two families comfortably. Hot Tub, fireplace, towels and linens. Sleeping space for up to 10. Close to shopping and to Interstate 91. Beautiful home to spend the winter season at!

    Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    197 Monadnock View Ln, Jamaica, VT 05343
  • /48

    $7,000 per month

    • 5 Beds
    • 3.5 Baths
    • 3,858 Sq Ft
    • House for Rent

    20 Jamie Ln, Winhall, VT 05340

    Escape to the tranquility of Vermont with this stunning long-term rental at "Valley View." Nestled in a desirable neighborhood of Winhall, this spacious contemporary home offers unparalleled panoramic views of the surrounding mountains. Imagine waking up to the beauty of the Green Mountains every day in this expansive retreat!This meticulously maintained 5-bedroom, 3.5 bathroom home

    David Powers 42 North LP

    20 Jamie Ln, Winhall, VT 05340
  • /46

    $5,000 per month

    • 3 Beds
    • 3.5 Baths
    • 2,300 Sq Ft
    • House for Rent

    15 Nearing Rd, Winhall, VT 05340

    Imagine waking up to inspiring vistas every day in this remarkable 3 bedroom, 3.5 bath saltbox home. Perched to capture stunning panoramic views of Stratton Mountain's trails, this classic contemporary ski home offers a truly special living experience. The property is settled upon a 1.63-acre knoll and abuts the Winhall Forest, offering peace and privacy.Embrace sustainable living with a

    David Powers 42 North LP

    15 Nearing Rd, Winhall, VT 05340
  • /8

    $2,850 per month

    • 3 Beds
    • 1.5 Baths
    • 1,500 Sq Ft
    • House for Rent

    176 Harrington Rd, West Townshend, VT 05359

    SUMMER SEASONAL RENTAL!!Charming well kept log home tucked away in a country setting in Windham. Centrally located between Chester, Grafton and Londonderry. A great getaway to enjoy all of what VT has to offer (summer activities, wildlife and hiking trails to name a few). Fully furnished and all inclusive for $2,850.00 per month. Tenant pays trash removal. Available July 1, 2025 thru

    Team BVA Rentals Barrett and Valley Associates Inc.

    176 Harrington Rd, West Townshend, VT 05359
  • /20

    $28,000 per month

    • 2 Beds
    • 1 Bath
    • 660 Sq Ft
    • House for Rent

    12 Seneca Dr, Queensbury, NY 12804

    Extended Summer Rental | June 28 - September 5 | $28,000Spend the summer at this charming 2-bedroom, 1-bath lakeview cottage in the desirable Takundewide Association, Cleverdale. Available from June 28 through September 5, this fully furnished home sleeps 4 and features a well-equipped kitchen and a screened porch—perfect for enjoying your morning coffee.Community amenities

    Kristine Owen Owen & Associates Real Estate

    12 Seneca Dr, Queensbury, NY 12804
  • /32

    $14,000 per month

    • 4 Beds
    • 2.5 Baths
    • 2,600 Sq Ft
    • House for Rent

    14 Burnt Hill Rd, Winhall, VT 05340

    This modern Strattonwald gem is the ultimate plug-and-play Vermont summer house with location, style, convenience and a lake-side lifestyle to remember. Three living spaces -- one on each floor -- allow for plenty of overflow in the morning and afternoon, with two fireplaces ready for friends and family. Four bedrooms plus sleep loft with its own hang-out space lend space for the whole crew!

    Jamie Luke TPW Real Estate

    14 Burnt Hill Rd, Winhall, VT 05340
  • /40

    $40,000 per month

    • 3 Beds
    • 2.5 Baths
    • 4,007 Sq Ft
    • House for Rent

    975 S Hill Rd, Ludlow, VT 05149

    Come enjoy your ski season at this exceptional home located on prestigious South Hill. Pull right into the heated attached garage (no need for cleaning off the car on powder days!) then step into the big mudroom where you can store all of your gear, with washer/dryer and powder room. Now into the eat in kitchen with beautiful wood cabinetry and floors. The formal dining room is perfect for a nice

    Frank Provance Diamond Realty

    975 S Hill Rd, Ludlow, VT 05149
  • /32

    $4,000 per month

    • 3 Beds
    • 3.5 Baths
    • 2,080 Sq Ft
    • House for Rent

    194 Main St, Grafton, VT 05146

    VACATION RENTAL. In the center of Grafton Village find the refined Phebe Frost house. Beautifully maintained and thoughtfully decorated, spend some special time in Vermont! Lovely features include wood floors, double sided fireplace in living and dining, comfortable family room/den and stocked pantry. Delightful master suite on main floor and two additional bedrooms bookend a full bath upstairs.

    Jessica Landers Barrett and Valley Associates Inc.

    194 Main St, Grafton, VT 05146
  • /11

    $1,750 per month

    • 1 Bed
    • 1 Bath
    • 600 Sq Ft
    • House for Rent

    214 Main St, Cavendish, VT 05153

    NOT AVAILABLE UNTIL AUGUST 18, 2025. Fully furnished & outfitted, including kitchen pots/pans/plates/etc. Convection oven, microwave/hood fan over. Full sized fridge. Front loading W/D. Walkable to shopping, restaurant. 10 minutes to Okemo, 25 minutes to the Killington Skyeship. School right up the street, so no amount of snow will keep you from the Mountains! VAST trail right up the street too!

    Robert Balewicz Evergreen Realty of Vermont

    214 Main St, Cavendish, VT 05153
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