Places to stay in Holyoke

Guest suite in Winchester

A two-story chalet-style house is framed by lush greenery and colorful landscaping. A gravel driveway leads up to the home, which features a welcoming porch with a decorative American flag. The first floor is supported by a lower level that includes outdoor amenities.

4.96 out of 5 average rating, 134 reviews

Private Suite 2 Bedroom Deck Lake Views

Welcome to “The Mermaid” at Highland Lake!!! Modern 2-bedroom private bath suite with kitchenette (see amenities) in the foothills of the Berkshires! Views of Highland Lake from your private sundeck. Moon and star gazing by night. We follow all Airbnb policies & State of CT COVID cleaning guidelines. Please do not trespass on the property of private residences, across the street on the lake side. These are private residences. There are public beaches public access areas for your enjoyment.

4.84 out of 5 average rating, 373 reviews

The exterior of the home is illuminated with warm string lights, enhancing the inviting ambiance. A spacious deck is visible, accompanied by a cozy seating area in the backyard, surrounded by lush greenery. The house features a classic design, with ample windows reflecting the evening light.

Home in Litchfield

Rustic - Modern - Hot Tub - Mohawk Mountain - BBQ

Enjoy the comfort of home with air conditioning, heating, dedicated workspace, TV, and Wi-Fi. Cook your meals in the fully-stocked kitchen with all the essentials. Pamper yourself in the private bathtub or shower with provided body soap, shampoo and conditioner. Relax in the hot tub or lounge in the backyard with an outdoor dining area, bbq, patio, and fire pit. 3 Min - Litchfield Town 4 Min - Arethusa Dairy farm 5 Min - White Memorial Conservation Center 16 Min - Mohawk Mountain Ski Area

4.96 out of 5 average rating, 226 reviews

An open-plan kitchen and living area is featured, with a large island bar and two stools. A cozy seating arrangement includes a dark gray sofa. Natural light enters through large windows, illuminating wooden floorboards and a neutral color palette.

Loft in Tolland

Cozy studio loft

Home away from home! In a serene, wooded area tucked away from the road, you'll find our studio loft mother-in-law apartment. Beautiful views with wildlife often spotted. Well-lit with many windows to let in the morning light. Suitable for a change of scenery while working remotely, a brief stay between locations, or your actual destination. UConn is minutes down the road. Looking for antiques? Stafford Speedway? Mohegan Sun or Foxwoods visits? Outdoor enthusiast? This place works for all!

Vacation home in Torrington

An open living area showcases high wooden ceilings with skylights, allowing natural light to fill the space. A simple seating arrangement includes a dark sofa and stylish chairs, while a light rug anchors a coffee table. Modern decor complements the neutral color palette.

4.95 out of 5 average rating, 203 reviews

Modern/Private Five ★ /Hotel quality stay/1 BR Apt

Enjoy the comfort and tranquility of this modern apt. A lovely space to relax after a busy day. This clean and bright apt offers a tranquil residential vibe alongside quick, easy access to the Torrington downtown areas, restaurants, stores and bars. It features an open-concept layout, a neutral color scheme, wood surfaces, tasteful furnishings and decor. Designed comfortably for your stay offering WiFi, Netflix, laundry, queen bed, well equipped kitchen, and clean fresh white bed sheets.

4.93 out of 5 average rating, 160 reviews

A modern bar area features a wooden counter with an array of glassware and liquor bottles. Behind the bar, shelves are stocked with various spirits. The warm ambiance is enhanced by soft lighting, while patrons socialize in the background, enjoying the intimate setting.

Cottage in Amherst

Beautifully Restored Cottage Studio

Originally built as an artist's studio, our Private Cottage is a fully-restored, light-filled, wonderfully serene space - with plush and thoughtful designer-appointed furnishings, cathedral ceilings, hardwood floors, a renovated en-suite bath, and a complete kitchen. Freshly laundered 450+ thread count Egyptian cotton beddings, linens, and towels are provided on-site as are complimentary amenities. * Fully Private, Quiet & Serene, Family-Friendly * An easy 3-minute drive to town

4.97 out of 5 average rating, 327 reviews

A serene outdoor space features a grassy area with two lounge chairs and a small table arranged neatly. A hammock is set nearby, surrounded by lush greenery and trees, providing a tranquil setting for relaxation.

Home in Holyoke

Explore Holyoke from this charming 3 Bedroom house

This house is settled in a quiet residential neighborhood.Guests have access to the entire second floor,one flight of stairs and you're in.There are lots of windows that brighten the space,with a large dining room,office desk, and a newly renovated bathroom.The living room leads to a beautiful spacious porch over looking the park/playground.All bedrooms have comfortable matresses,lots of pillows, soft sheets,thick super soft towels. Smart TV (Netflix/hulu/sling/roku)

4.92 out of 5 average rating, 153 reviews

A spacious bedroom features a green wooden bed dressed in white linen, flanked by large windows with sliding doors leading to a serene outdoor view. A comfortable armchair and a small side table are positioned nearby, adding to the cozy ambiance.

Home in Otis

The Pinnacle House at Otis Ridge Ski Area!

Otis is the best town for a visit to the Berkshires. It is close to all the places you would want to visit like Jacob's Pillow, Tanglewood, Norman Rockwell Museum to start with. It is also close to hiking trails, swimming, shopping and great restaurants. This wonderful three plus bedroom home is located on the backside of Otis Ridge Ski Area. Wake up and take a walk on the ridge or just sit outside and have your morning beverage with the woods surrounding you.

4.99 out of 5 average rating, 109 reviews

A patio area is set with a round table and four chairs under a large umbrella, offering views of the river. A grill is positioned nearby, and flower planters enhance the space. Lush greenery is visible across the water, framed by a clear blue sky.

Home in Canton

Best River View, on Rail Trail in Collinsville!

This quaint and spotless home is perched on a knoll across the road from the Farmington River & Rails to Trails you can walk to restaurants, gift shops & antique shops; Canoe/Kayak/Paddleboard; go fishing; enjoy the Farmington River Rail Trail; hiking trails, and Ski Sundown close by; or just relax & enjoy the view! Enjoy the best view in Collinsville - one of "America's 10 Coolest Small Towns" by Arthur Frommer's Budget Travel Magazine. Beautiful year round!

4.77 out of 5 average rating, 196 reviews

Apartment in Chester

Quiet getaway in the Berkshires

Very nice quite place Two floors must climb stairs 3 bedrooms very large master Fully equipped kitchen Two full baths and laundry area Deck off the kitchen with fire pit in the back yard Lots of hiking and skiing in and around the area or stay and relax Carm’s diner for a great Breakfast Chester Common Table for dinner or The Blue Note Cafe for Pizza and a drink or Call for some takeout and a convenient store for anything you forgot

Guest suite in South Hadley

A historic two-story house with a yellow exterior is surrounded by a green lawn and mature trees. A wide porch extends across the front, featuring white railings. A concrete walkway leads from the street to the entrance, offering a welcoming path to guests.

4.94 out of 5 average rating, 295 reviews

Charming 3BR | Private 2nd-Fl Escape Near MHC

Enjoy privacy and charm in this renovated 3-bedroom, 1-bath second-floor suite of our 1875 farmhouse! This peaceful retreat offers a private entrance, modern amenities, and easy self check-in. Walk to Mount Holyoke College and Village Commons, or take a short drive (less than 20 minutes) to Amherst and Northampton. Perfect for families, couples, or university visitors seeking a quiet, historic home away from home.

4.85 out of 5 average rating, 169 reviews

A serene riverside deck overlooks the calm waters of the Connecticut River. The space features wooden railings and is surrounded by lush greenery, with a few bare trees reflecting the change of seasons. The peaceful landscape offers a quiet spot for relaxation.

Cottage in Enfield

Hilda’s Riverside Retreat

Amazing Newly renovated Airbnb! Nestled along the meandering, Connecticut River, beautiful veiw! “Just what the doctor ordered”. And just a stone’s throw away from Downtown Springfield, MGM and Hartford. Whether you are visiting the Knowledge Corridor to visit any of the 30+ universities and liberal arts colleges, business or pleasure, This waterfront property is cozy and offers every amenity you left at home!

Guest suite in East Granby

A brick patio area is seen with two rocking chairs positioned beside vibrant orange and yellow flower pots. A welcoming wreath adorns the double doors, and a pumpkin is placed on the ground, enhancing the seasonal decor.

4.85 out of 5 average rating, 350 reviews

Staying at Ten Hillcrest

What I’ve always thought of as the perfect location! Private enough to see trees and birds and yet close enough to jump on the highway to anywhere. Conveniently located on a dead end street with no through traffic. On your way out take a left and head towards farm and eateries or take a right and head to the city of Hartford or Springfield. Just minutes from Bradley International Airport

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

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A space thats all yours, with room for everyone

Hotels

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Popular amenities for Holyoke places to stay

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Holyoke's top sights

Mount Tom State Reservation41 locals recommend

Holyoke Mall31 locals recommend

Coco and The Cellar Bar28 locals recommend

Small Oven Bakery25 locals recommend

Luthier's Co-Op19 locals recommend

Abandoned Building Brewery19 locals recommend

Other great vacation rentals in Holyoke

4.91 out of 5 average rating, 144 reviews

A sandy beach area borders a calm pond, featuring five white Adirondack chairs positioned on the shore. A floating wooden platform with a slide extends into the water, surrounded by lush green trees that provide a serene backdrop.

Guest suite in Granby

Whole place,staycation,3 bedrooms, spacious area

4.99 out of 5 average rating, 103 reviews

An outdoor seating area features five black Adirondack chairs arranged around a fire pit, with flames visible inside a round, metal enclosure. The cabin's two balconies are illuminated from within, surrounded by trees displaying autumn foliage.

Cabin in Sandisfield

Berkshires Cabin in Woods with Mountain Views

4.93 out of 5 average rating, 100 reviews

The exterior of a rustic two-story home is surrounded by lush green grass and a variety of trees and flowering shrubs. The house features dark wooden siding and large windows, while a stone patio is visible in the background, framed by natural landscaping.

Home in Shelburne Falls

Buckland House - A World Apart

4.96 out of 5 average rating, 108 reviews

Home in Otis

Direct Lakefront Home on Otis Reservoir Giant Yard

4.85 out of 5 average rating, 310 reviews

An outdoor deck features a hot tub, providing a relaxing space. Comfortable seating is arranged with turquoise cushions around a central fire pit. A gas grill is positioned nearby, and a shade sail provides coverage from sunlight. The surrounding neighborhood is also visible.

Townhouse in Easthampton

In style row house with private hot tub/pool table

Guest suite in Easthampton

The image captures a panoramic view of a lush, green mountain range under a bright sky. Wispy clouds stretch across the sky, creating a dynamic backdrop to the vibrant foliage below.

4.92 out of 5 average rating, 259 reviews

The Floating Library: private hiker's hideaway

4.96 out of 5 average rating, 118 reviews

Home in Bloomfield

Spacious Charming New England Cape