Guest house holiday rentals in Pioneer Valley

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Top-rated guest house rentals in Pioneer Valley

Guests agree: these guest house rentals are highly rated for location, cleanliness and more.

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Top guest favourite

A spacious living area features modern seating arrangements with natural light streaming through large glass windows. A small table is set by the window, overlooking the garden. Polished wooden floors and decorative items add warmth to the inviting atmosphere.

Guest house in Marlboro

Refined, serene and like no other, Marlboro, VT.

Our elegant, supremely comfortable, and private guesthouse is surrounded by a wonderful garden and 350 acres of woodland in the quiet of rural Vermont. We are 30 minutes from Brattleboro to the east, with its many shops and restaurants, and 12 minutes from the small town of Wilmington to our west, with some restaurants, shops, and a supermarket However, we always recommend bringing groceries, etc., for your first night and next morning. We are pleased to offer a 20% discount for 7 days or more!

4.97 out of 5 average rating, 188 reviews

Top guest favourite

The entrance features a white door with a windowpane design, framed by light blue siding. A decorative lantern hangs beside the door. A small potted plant rests on a blue chair, while a welcome mat adorned with black dogs is placed at the threshold.

Guest house in Northampton

Mill River Cottage (pet friendly!)

Welcome to our peaceful and unique urban farm cottage. We are located in historic Florence, Massachusetts (a part of Northampton). While our place is no longer a working farm, the cottage was created many years ago to support the main dwelling. It has been modernized to offer every comfort while maintaining its cozy aesthetic. Free parking & lighted access to the cottage. The cottage is a private space where you can come and go as you please. Relax and unwind or head out to explore the area!

5.0 out of 5 average rating, 437 reviews

Top guest favourite

A spacious studio is illuminated by natural light from large windows. The bright room features a mix of furnishings, including a white sofa, a dining table, and a variety of shelving units. Warm wood flooring complements the inviting layout.

Guest house in Northampton

Large Eco-friendly Studio – Walk to Town

★ Superhost for 12 years — a unique loft-style studio, surrounded by beautiful gardens, a short walk to town and Smith College. Perfect for visiting the colleges, attending weddings, workshops, or a peaceful stay away to work or write, close to hiking and bicycle trails. Before requesting a reservation, please send a quick message first. We respond fast to make sure the unique space is the right fit for you — we just like to say hello first! Read on to see if it sounds like your kind of stay.

4.93 out of 5 average rating, 307 reviews

Top guest favourite

Guest house in Cummington

Cozy Hilltown Cottage

Enjoy a peaceful stay in this cozy, creative space. Set on 10 acres of gardens and woods, this cottage is perfectly located to explore Western Massachusetts - with places like MASS MoCA, Shelburne Falls, Tanglewood and Northampton all within a 30min to 1 hour drive. Upstairs is a queen bed and full bath, while downstairs features a functional kitchen, work desk, grand windows, and a living space with full sleeper sofa. We live in the main house on property but respect your privacy-see photos!

4.99 out of 5 average rating, 220 reviews

Guest favourite

A charming kitchenette is showcased with colorful cabinetry and floral wallpaper. Pendant lights hang above the counter, illuminating the space. A dining area with two chairs and a small table is visible, while decor items add character to the walls and shelves.

Guest house in Vernon

Cozy private one bedroom guest apt suite

Centrally located, just minutes from I84, 20 min to Uconn, 15 min to capital of Hartford, 1 hour drive to Cts famous casinos, 30 min to MGM Springfield, enjoy local dining close by. Private entrance guest suite with parking for one vehicle at your door. Private bedroom with double bed and pull out sofa in living room area, workspace, smart tv, internet ready, kitchenette with fridge, microwave, 2 burner cooktop, and coffee maker, snacks and refreshments, linens, some toiletries available

4.87 out of 5 average rating, 185 reviews

Guest favourite

Guest house in Enfield

Close AirPort|SixFlags|Big E|Free Private Parking

Escape to Pineside Retreat in Enfield, CT—a tranquil haven blending comfort and nature. Conveniently located 20 minutes from Bradley Airport and MGM Springfield Casino, 15 minutes from Six Flags, 22 minutes from Holyoke Mall, 5 minutes from Scantic River State Park, and 10 minutes from Windsor Locks Canal State Park. Perfect for professionals or adventurers seeking relaxation in a cozy, rustic-modern retreat. Per-person pricing. Please select the correct number of guests when booking.

4.94 out of 5 average rating, 100 reviews

Guest favourite

A modern, renovated barn is set against a backdrop of lush greenery. Two brightly colored lounge chairs and a reclining chair are positioned on the grassy area, inviting relaxation. Large windows reflect the surrounding trees, emphasizing the tranquil outdoor setting.

Guest house in Stockbridge

Modern barn in the heart of the Berkshires

Modern, renovated dairy barn in the heart of the Berkshires. Located on 3.5 acres with beautiful views and close to everything. 1.5 miles to Main St Stockbridge/Red Lion Inn, 5 minutes to Tanglewood, 5 minutes to the Stockbridge Bowl and beautiful hiking trails, under 10 minutes to Lenox . This is the perfect base for exploring the Berkshires or a great getaway for relaxing and enjoying nature. Family and pet friendly! *Please read Interaction with Guests section before booking*

4.91 out of 5 average rating, 171 reviews

Top guest favourite

Guest house in Amherst

Cozy get-away!

This quiet option is less than two miles from the center of downtown Amherst, a thriving college town with museums, libraries, small stores, restaurants for every budget, hiking trails galore. We offer a relaxing, TV-free space in a friendly, safe, residential neighborhood. Five minute walk to 2 bus stops. If you are looking for some privacy with access to western Mass., you've found it!

4.96 out of 5 average rating, 723 reviews

Top guest favourite

The charming stone cottage features a vibrant blue door and flower boxes filled with colorful plants. Lush greenery surrounds the entrance, and original brick walkways lead to the home. Sunlight filters through the trees, creating a welcoming atmosphere outside.

Guest house in Granby

Windy Top Cottage ~ A Romantic "European" Getaway

The Windy Top Cottage is an old stone building constructed in 1932 by H. L. Bitter, a wealthy Hartford businessman. This area of Granby was a favorite of the Hartford elite for a place to 'summer' in the early part of the 20th Century. The cottage was the quarters for the domestic staff while the family was in North Granby. With an elevation of 970, we offer clean, fresh country air!

4.98 out of 5 average rating, 928 reviews

Guest favourite

The exterior of the studio space is visible, featuring a natural wood façade enhanced by a mural depicting a serene landscape with sailboats on water. Large windows are present, allowing for natural light. Surrounding greenery contributes to a tranquil atmosphere.

Guest house in Belchertown

Amherst Area Studio Apartment

Convenient location on quiet side road near Amherst, Hampshire, and UMass. Easy commute to Smith and Mt. Holyoke. Unique 2nd floor open studio space with 1 single and 1 dble bed, a sofa and chair, a dining nook with a small kitchenette + full bath. Bathroom is on first floor but studio is on second floor. Public beach is available June 24 and is steps away!

4.91 out of 5 average rating, 204 reviews

Top guest favourite

A gentle brook flows through a landscape adorned with autumn leaves. Tall trees line the banks, their foliage transitioning to various shades of gold and orange. Smooth stones are scattered in the water, and the ground is covered with a carpet of fallen leaves.

Guest house in Williamstown

Brookside Cottage

Drift off to the sound of a babbling brook outside the bay window in this cozy country cottage. Minutes from Downtown Williamstown, North Adams and Bennington, VT. We are about 20 minutes away from Jiminy Peak for downhill skiing. The trails behind our house are ideal for snowshoeing, nordic skiing, and snowman building.

4.96 out of 5 average rating, 231 reviews

Top guest favourite

Guest house in North Adams

Netherwood - North Adams Guest House with Views

Stay at Netherwood in a classic New England carriage house converted into a guest house with modern amenities, including king beds and en suite bathrooms. Private with amazing views, yet readily accessible to local attractions. Please indicate the number of suites you will need (1, 2, or 3).

5.0 out of 5 average rating, 336 reviews