Places to stay in Springfield

Apartment in Windham County

An orange front door is framed by a simple metal railing and concrete steps, leading to the entrance of the Woodpecker's Nest. Sunlight casts shadows on the textured surface of the steps, contributing to the inviting atmosphere.

4.96 out of 5 average rating, 45 reviews

Woodpecker’s Nest

With 15 acres of private wooded land, count on High Speed Wi-Fi throughout the Woodpecker's Nest if you work from home or just need to catch up on emails! Coffee bar is stocked, have a cup taking in an ideal view of the woods! Television is ready to stream movies with family & friends! Plenty of indoor & outdoor seating for meals as you watch the sunrise or sunset cast pink hues over the woods & sky! As the sky darkens & the stars light up, gaze up in wonder in a very quiet area of New England!

4.99 out of 5 average rating, 127 reviews

Home in Woodbury

Your Perfectly Wonderful Woodbury Sanctuary!

Just 90 minutes from NYC, this Getaway is Perfect! Antiques, photographs, & sculptures fill this sanitized, rambling, relaxing, light-filled 2 story 4 bedroom 2.5 bath on Connecticut's Antique Trail. All 2,800 sq. ft of my home is at your disposal and 2 minutes from 5 popular, fabulous restaurants. Your Host lives in the attached Artist Studio with its own access and parking. Stay here and you may agree with Reader’s Digest magazine that "Woodbury is Connecticut's Most Charming Small Town."

4.98 out of 5 average rating, 135 reviews

A serene indoor hot tub is surrounded by wooden paneling and natural stone accents. Soft blue lighting illuminates the water, while greenery is positioned nearby, enhancing the calming ambiance of the space.

Condo in Norwich

The Vacay Villa

The Vacay Villa, just minutes away from Mohegan Sun, Foxwoods and The Spa at Norwich Inn, offers so many amenities you won’t even have to leave the grounds. Private balcony, fireplace, two outdoor pools currently open, year-round access to luxurious hot tub and saunas, small workout room, laundry facilities, pub and upscale restaurant allow for a one-of-a-kind stay at an incredibly affordable price. Why spend hundreds to stay at the area casinos when you can stay in your own private villa?

4.96 out of 5 average rating, 104 reviews

A winter scene depicts a charming town square with snow-covered ground, featuring a building adorned with a glowing Christmas tree in its window. Vintage cars are parked in front, while small groups of people are visible, creating a festive atmosphere against a twilight sky.

Apartment in Stockbridge

Historic,Famous,Iconic, Unforgettable Berks Escape

PICTURE IT...You can put yourself in the "famed" Norman Rockwell Main Street at Christmas Painting! That's Right,Cozy, Intimate,Magical and all to yourself.Fully equipped with all the comforts of home. Small Town Charm,Big time Historic setting in the heart of Downtown Stockbridge! Spend your afternoon sipping Tea or Wine looking out the iconic picture window Norman Rockwell installed himself. The one where the Christmas Tree Glows in a room that was Norman Rockwell's Studio from 1953-1957

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, 204 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, 161 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

4.88 out of 5 average rating, 34 reviews

A charming private estate is illuminated at dusk, showcasing a spacious house with multiple gables and a covered porch. The landscape features a gravel driveway bordered by lush greenery and decorative stone walls, creating a welcoming atmosphere.

Guest suite in Ledyard

Stylish Loft w/ Organic Breakfasts & Scenic Hiking

This Loft is in a perfect location for enjoying Mystic, Connecticut, area wineries, casinos, beaches, museums, and fine dining. Located on a very private countryside estate, this lovely, bright, and breezy loft space has a beautiful whitewashed pine ceiling with lots of windows and a private balcony, so you can enjoy looking out over the trees and gardens. With blackout shades, you can comfortably rest as late as you want. Come and go as you like with your own private entrance.

Guest suite in Charlemont

A spacious interior is displayed, featuring a living area with comfortable seating and two beds. Large windows allow natural light to fill the space, enhancing the inviting atmosphere. Decor elements include artwork and cozy textiles, creating a homely environment suitable for relaxation.

4.91 out of 5 average rating, 207 reviews

Unique People & Pet-Welcoming Haven

Your own gracious living space with very well equipped kitchen, private deck, entrance, garden, country roads for dog walks, forests, meadows, mountain streams, stone walls, tranquility. The cottage is attached to the main house but is a "separate" entity and again has its own private entrance as mentioned above. No smoking in the cottage please but on the deck just fine. There is an air purifier that runs 24/7. Wi-Fi signal is strong and reliable. MA Taxpayer ID: 10352662

4.92 out of 5 average rating, 172 reviews

A well-lit outdoor space features string lights overhead, illuminating a patio area. A set of lounge chairs is positioned beside a small table, with an umbrella providing shade above. Stairs lead to an upper deck, enhancing the outdoor living experience.

Home in Bristol

Cozy Family Home - Kid & Pet Friendly

3 bedroom house on a quiet street. 5mins down the road from ESPN and Lake Compounce. Kid friendly. Pet friendly. Workspace available. 1 bedroom w/ king bed. 1 bedroom w/ queen bed. 1 bedroom w/ 2 twin beds. Fully finished basement with 60inch TV, kids toys and fitness equipment/stationary bike. Deck and below deck hang out space. Though we aren’t living here full time, it’s still the place we call home, and we will use it when it’s not booked. Long stays welcome.

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!

A staircase leading downward is showcased, featuring dark wooden steps with a carpet runner. The walls are painted in a soft grey tone. A white door at the bottom leads outside, framed by a welcoming light fixture above. A small welcome mat is positioned at the entrance.

5 out of 5 average rating, 44 reviews

Downtown 2 BR 1.5 Bath Townhouse Retreat 3 beds

Conveniently located townhouse that is a short walk to restaurants and shops. Easy access to public transportation with a bus stop by the end of the street. Wi-Fi, a full kitchen, living room, 1/2 bath and laundry, on the first floor. The second floor has a shower, bedroom #1 has a queen bed and bedroom #2 has a queen and a twin. A/C units during summer months. Off street parking and self check in. Pack n play and toddler bed available upon request.

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!

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Popular amenities for Springfield places to stay

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Springfield's top sights

Regal MGM Springfield 744 locals recommend

Springfield MGM Casino station41 locals recommend

Fletcher's Brooklyn Barbecue28 locals recommend

Stop & Shop27 locals recommend

Red Rose Pizzeria13 locals recommend

MassMutual Center10 locals recommend

Apartments in Springfield

4.94 out of 5 average rating, 149 reviews

Apartment in Stafford

Modern Industrial Apartment with rooftop access

4.85 out of 5 average rating, 133 reviews

The exterior of a two-story blue apartment building is depicted, featuring a covered porch and welcoming entrance. Two parked cars are visible in the driveway, with green lawns and trees nearby. Window flower decorations add a touch of charm to the façade.

Apartment in Adams

full apartment in adams self check in

4.91 out of 5 average rating, 129 reviews

The living area features a plush sofa adorned with decorative pillows, accompanied by a vintage armchair and a small wooden side table. A soft area rug covers the floor, while natural light filters through the window, which has blinds for privacy.

Apartment in Lenox Dale

Charming 2BD apartment.

A cozy living space features a yellow loveseat adorned with patterned pillows, positioned next to a glass coffee table. Natural light filters through sheer curtains, illuminating the wooden floor and a decorative area rug. A small side table stands nearby.

4.97 out of 5 average rating, 348 reviews

Light filled three bedroom apartment DT Florence!

4.91 out of 5 average rating, 259 reviews

The exterior of a charming house is framed by vibrant autumn foliage, including trees with bright yellow and red leaves. A stone chimney adds character to the roof, while a wooden fence borders the well-maintained garden. Soft light highlights the warm colors of the scene.

Apartment in Amherst

Amherst, Quiet, Private, Cozy Studio Apartment

4.84 out of 5 average rating, 129 reviews

The updated kitchen features modern appliances, including a black microwave and oven. Light-colored cabinetry contrasts with the granite countertops. A coffee maker sits on the counter, and a dining table is visible, providing a space for meals. The floor is covered with wood-like laminate.

Apartment in Holyoke

Quiet bright & sunny 2 bedroom apartment w/ porch

A spacious living area features wooden flooring and a mix of seating options, including a dining table and comfortable chairs. Light streams through large windows, highlighting the high ceiling with exposed beams. Decorative elements like area rugs and wall art contribute to the inviting ambiance.

4.85 out of 5 average rating, 748 reviews

Down town Florence Temperance Hall

A spacious living area features a large leather couch with button detailing and a wooden side table beside it. Natural light filters through two windows adorned with light-colored curtains, highlighting the warm tones of the hardwood floor.

4.99 out of 5 average rating, 208 reviews

Skylights, art + design in best downtown location

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Other great vacation rentals in Springfield

4.93 out of 5 average rating, 319 reviews

A covered outdoor seating area features a combination of woven chairs and a sofa arranged around a stone floor. Soft lighting is provided by string lights overhead, while rustic wooden beams and walls create a warm, inviting backdrop.

Guesthouse in Southbury

Charming Guest Cottage with Modern Amenities

4.89 out of 5 average rating, 135 reviews

A comfortable living area features a cozy seating arrangement with a blue sofa and an inviting armchair, set against a rustic stone fireplace. A warm light emanates from above, illuminating the wood-paneled ceiling and vibrant area rug. Large windows allow natural light to fill the space.

Cottage in Hebron

Welcome to The Holly at Amston Lake

4.77 out of 5 average rating, 197 reviews

Apartment in Chester

Quiet getaway in the Berkshires

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!

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

4.97 out of 5 average rating, 115 reviews

A spacious deck features several lounge chairs and a table, inviting relaxation. A bright red umbrella provides shade. The tranquil lake extends in the background, with a private dock visible along the shoreline, framed by lush greenery.

Home in Pittsfield

Berkshire Lake- Modern and Updated-close to skiing

4.89 out of 5 average rating, 399 reviews

A welcoming display includes two wine glasses beside a bottle of wine on a granite countertop. A wicker basket holds assorted snacks, while a blue candle and a bouquet of white tulips add a touch of elegance. An information guide is also visible.

Villa in Norwich

Peaceful Spa Escape minutes to Mohegan Sun Casino