Vacation rentals in Pittsfield

4.98 out of 5 average rating, 146 reviews

A log home features a spacious deck overlooking the lake, with seating areas and a hammock. Large glass windows provide a view of the serene outdoor space, including a manicured lawn and easy access to a wooden dock.

Apartment in Fairlee

Kismet Cottage, Perfect for longer stays

Welcome to your home away from home! This charming, fully-furnished 1-bedroom apartment sits right on the lake, offering serene views and a peaceful retreat after a long shift. With four major hospitals located within a 30-minute commute, this is the ideal spot for traveling nurses looking for comfort and convenience. Everything you need is here from a cozy queen bed to a fully equipped kitchen and comfortable living space including a laundry room so you can stay fresh and ready for your shifts.

5 out of 5 average rating, 5 reviews

A serene outdoor space features two Adirondack chairs positioned around a fire pit, surrounded by lush green grass and a backdrop of dense trees. The calming natural setting invites relaxation and outdoor gatherings.

Cottage in Mendon

The Mendon Cottage: Cozy Home. Killington / Pico

Recently renovated 2BR/2BA cottage in Mendon, VT, near Pico & Killington Ski Resorts, & Rutland. Sleeps 6: 1BR w/ queen & ensuite, 2nd BR w/ 2 double beds. Additional BA, laundry room, living room w/ smart TV, fully equipped kitchen & dining area. High-speed WiFi, mini splits for heat/AC, front & back decks, BBQ grill. All new furnishings offer modern comfort & rustic charm. Ideal for skiing, exploring, or relaxing in the mountains. Perfect base for your VT adventure! Discounted ski rentals.

4.89 out of 5 average rating, 9 reviews

A grassy area features a fire pit surrounded by several white Adirondack chairs. A large tree provides shade beside the inviting white house, which has multiple windows and a porch. Scenic views of the landscape are visible in the background.

Home in Poultney

Snowberry Farm Home Sweet Home

This memorable place is anything but ordinary. Hike the hayfields on the mowed paths! Fish in the Pond and enjoy the peace and quiet of this comfortable and spacious home. Star gazing is on the menu too! One mile to rail trail for bike enthusiasts. This house is very welcoming & well equipped for entertaining family & friends. Room for everyone & extra space for quiet reading & conversation. Cider house, craft breweries, dining options& golf all nearby. Escape Florida or Arizona summer heat!

4.91 out of 5 average rating, 100 reviews

Cabin in Bridgewater

100 Acres Views & Creek near Woodstock/Killington

You will leave the demands of your busy lifestyle behind when you vacation on our 100+ acre 4 BR 2 BA cabin property with a babbling crystal clear mountain creek. Place your beach chair in the creek, relax with your favorite book for Best Spa Experience Ever! Large open covered porch with porch swing seating to enjoy the expansive mountain views, listen to the leaves rustle and the stream running in the distance. Miles of hiking & biking trails, skiing, restaurants and more nearby.

4.95 out of 5 average rating, 19 reviews

Home in Enfield

Upper Valley Shaker-Style Home, close to Dartmouth

Located within minutes to Dartmouth Health Medical Center and Dartmouth College, this home offers a comfortable, warm place to gather with friends and family during your visit to the Upper Valley. Just off Route 4, this home offers easy access to I-89 and I-91. This home is unique in its location and proximity to Mascoma Lake. A common right of way and short walk will lead you to the lakefront park and rail trail, where the views are breathtaking. Snowmobile access to rail trail

5 out of 5 average rating, 10 reviews

A waterfront home is surrounded by lush greenery, featuring a large deck with multiple seating areas. A small blue paddleboat is visible on the lake, alongside a spacious dock equipped with Adirondack chairs. A calm, reflective water surface complements the serene environment.

Cottage in Croydon

Charming Lakefront cottage with beautiful views

Make memories with family or friends at our perfectly situated waterfront getaway. Enjoy the tranquility of waking up to peaceful mornings with a cup of coffee on your bedroom balcony. Take a leisurely tour of the lake in our kayaks or paddleboat. In the evenings, enjoy toasting smores on the camp fire. Our spacious dock is great for fishing or sitting in the Adirondack chairs with your favorite beverage. We look forward to offering our guests a vacation to remember.

4.97 out of 5 average rating, 33 reviews

A modern kitchen features wood cabinetry and stainless steel appliances. A polished countertop provides ample workspace, while a multiple-burner stove and microwave cater to cooking needs. Natural light enhances the room through a nearby window, complemented by patterned curtains. A trash can and sink are also visible.

Apartment in Pittsford

Norm's Place

Located in historic Pittsford Vermont, come stay in our newly renovated private unit. Close to Killington and Pico for skiing, the Mountain Top Inn , The Brandon Inn and Lilac Inn for weddings and events. Walking distance to the Pittsford Recreation center and walking trails. Convenient to swimming at the Chittenden reservoir or State Parks. Lots of opportunities for hiking and experiencing local breweries. Come see what our beautiful state has to offer!

4.96 out of 5 average rating, 225 reviews

A spacious wooden house features a balcony with a railing, overlooking a green lawn. Large windows allow natural light to fill the interior, while five skylights add brightness. Vibrant trees display autumn foliage in the surroundings, creating a serene atmosphere.

Home in Addison

Brthtkng New Premier Lake Champlain Wfrnt Escape!

7/19/20 : UPDATE - We are fully compliant with all local, state and federal safety protocols. Call /text Us fir any questions, at 978-502-6282 . Be Well, Be Safe & We Look Forward to Having You as Our Guests! We are the #1 Premier Lake Champlain Breathtaking New Property with 250'+ Prime Lake Champlain West/Sunset/Adirondack Mtn. facing w/Amazing Sunsets & Jacuzzi Tub in Master Bath Overlooking Lake,Mountains & Amazing Sunsets and 250+ 5 Star Reviews!

4.96 out of 5 average rating, 26 reviews

A newly renovated New England cape is surrounded by a winter landscape, with snow covering the ground and tree branches. The dark grey house features a vibrant red front door, flanked by two windows and decorated with subtle holiday accents.

Home in Cavendish

3BR 1Bth New England Cape - Experience Vermont!

Relax with the whole family, or friends at this peaceful place to stay. Close to many local ski resorts, hiking trails, trophy fishing in the Black River off Route 131! Close to Ludlow And Historic Windsor and Woodstock VT! Only a 10 minute drive to Okemo Mountain and Jackson Gore! 30 Minutes to Killington Mountain and Magic Mountain 40 Minutes to Bromley Mountain Accessible to the natural beauty of Vermont!

4.78 out of 5 average rating, 9 reviews

Apartment in Warren

Professionally Managed Ski Gem

New listing! Come de-stress in the beautiful mountains of Vermont. Our condo and all the amenities included are perfect for a romantic getaway or a family vacation. Located less than a half mile from Sugarbush Resort, our condo is an ideal location for a ski vacation. However, the access to 3 pools, 2 hot tubs, tennis courts, basketball court, gym and more make this a perfect 4 season rental as well!

4.8 out of 5 average rating, 10 reviews

A spacious family room features a large, light-colored couch and a cozy area rug. A stone fireplace serves as the focal point, surrounded by large windows that provide a view of the wooded surroundings. A coffee table and an armchair enhance the inviting atmosphere.

Home in Hartford

Pet-Friendly, Mountainside Home | Treetop Lodge

Our vacation home is the ultimate getaway for families and groups looking to indulge in luxurious comfort and endless entertainment options. Book your stay today and experience the beauty and tranquility of this truly remarkable property. Please SEE: Other Things to Note For Area Details, Please SEE: The Neighborhood & Getting Around *Pet Friendly, fee applies per pet. *Includes Quechee Club Access

4.92 out of 5 average rating, 25 reviews

Cottage in Shoreham

Breathtaking, waterfront rental on Lake Champlain

Our secluded spot in the quaint town of Shoreham, Vermont will be sure to feel relaxed, rejuvenated, and ready to book your next stay. With 3 newly renovated cottages, our guests feel at home from the moment they step onto the property. With outstanding views and breathtaking sunsets overlooking the Adirondack Mountains, we all can't get enough of Watch Point.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Pittsfield vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Pittsfield's top sights

Clear River Tavern10 locals recommend

Original General Store11 locals recommend

Vermont River Tubing4 locals recommend

Other great vacation rentals in Pittsfield

5 out of 5 average rating, 12 reviews

An Adirondack style camp sits surrounded by trees, with a view of the lake in the distance. Clear blue skies are visible, and natural stone and wood accent the exterior. A pathway lined with greenery leads to the entrance of the home.

Home in Wells

Breathtaking Lakeside Retreat!

4.75 out of 5 average rating, 92 reviews

An outdoor pool is surrounded by lounge chairs and red umbrellas. Lush green trees frame the space, creating a serene environment. A small poolside shed is visible, adding functionality to the area.

Condo in Killington

Still 89 Trails Open, Low, Low Rates

4.86 out of 5 average rating, 35 reviews

A spacious estate is surrounded by a pristine winter landscape, featuring snow-covered grounds and towering trees. The residence showcases a distinctive architecture, framed by distant mountains under a bright blue sky. The outdoor space invites exploration and enjoyment of the snowy scenery.

Home in Manchester

Your VT Dream House: Fireplace, Pool, Dogs

4.9 out of 5 average rating, 88 reviews

A firepit surrounded by red adirondack chairs is placed on a snowy lawn, with a cozy fire burning in the center. The two-story retreat is visible in the background, featuring expansive windows and solar panels on the roof, all under a clear blue sky.

Home in Newport

Berry Mountain Lodge: Mountain Views by Lake & Ski

5 out of 5 average rating, 8 reviews

A warm hot tub is presented against a snowy landscape, surrounded by trees bare of leaves. The distant view of the reservoir is framed by the serene white of winter, inviting relaxation and tranquility.

Home in Chittenden

Modern Retreat next to Mountain Top Inn,Killington

5 out of 5 average rating, 16 reviews

The modern wooden exterior of the home features large windows that allow natural light to brighten the interior. A spacious deck extends from the second floor, surrounded by lush green grass and colorful autumn foliage.

Home in Plymouth

Luxury Modern Cabin near Okemo & Killington

4.97 out of 5 average rating, 39 reviews

A spacious hot tub emits a soft blue glow in the dark, surrounded by mist. The area is accented with a wooden deck, and a staircase provides access to the tub. Soft lighting enhances the peaceful ambiance of the outdoor space.

Home in Warren

Private Home with Hot Tub 1 mile from Sugarbush