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Places to stay in Springfield

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Top-rated places to stay in Springfield

Guests agree: these places to stay are highly rated for location, cleanliness, and more.

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Top guest favorite

Home in Woodbury

4.99 out of 5 average rating, 127 reviews

Your Perfectly Wonderful Woodbury Sanctuary!

GarrickRating, 5 stars1 week ago

Very comfortable house with a chef's kitchen, spacious bedrooms and living and dining areas, and pretty yard with lots of flowers. Doug has a fabulous collection of his own sculptors and very interesting photography. He is a very gracious 5 star host.

Top guest favorite

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

4.98 out of 5 average rating, 135 reviews

The Vacay Villa

JamieRating, 5 stars1 week ago

Krista place is very clean and welcoming. It had perfect personal touches. From coffee creamer for our morning coffee, to shower essentials. I find the small personal touches so nice and it is welcoming. Christa offered east check in and extended my check out time with no questions ask. This was a very nice place for a weekend trip and we will def be booking again!

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

4.96 out of 5 average rating, 104 reviews

Historic,Famous,Iconic, Unforgettable Berks Escape

ReganRating, 5 stars3 months ago

Theresa’s beautiful Norman Rockwell studio was so much better than I could have imagined! She was so thoughtful from start to finish with clear and easy communication about everything. Parking was very easy and you will clearly have a space right behind the building. The large picture window in the middle of the living room with a Christmas tree in the center was so lovely and heart warming! Very quiet yet steps from shopping and restaurants (the best breakfast in town can be had at Main Street Cafe downstairs!) I would highly recommend this charming apartment for anyone wanting a charming experience in Stockbridge. 10 out of 10!

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.

Vacation home in Torrington

4.95 out of 5 average rating, 204 reviews

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

CharlieRating, 5 stars5 days ago

Very nice accommodation. Everything was as described. Clean, bright, roomy, with laundry, private entry with parking spot right in front. I wasn't sure how lockboxes worked but I called when I arrived and Yivel answered immediately and told me how those work. We will definitely stay there again if the need arises!

A well-lit bedroom features a black wooden bed with a plush blanket layered over crisp white linens. A small bedside table holds a lamp, and framed photos adorn the walls. A window with a blackout shade allows natural light while a wooden chair adds a touch of warmth.

Home in Sheffield

4.91 out of 5 average rating, 117 reviews

Wow! Best BERKSHIRE SnowHome #1 Private SuperClean

FeliciaRating, 5 stars2 months ago

Sally responded to questions right away. She was really attentive - making sure snow was cleared and ice salted so that we could leave early in the morning after a big snow storm. The place was really conveniently located 15 minutes from ski Butternut. And it was immaculately clean and so cozy. It was a really nice stay.

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.

Guest suite in Charlemont

4.91 out of 5 average rating, 208 reviews

Unique People & Pet-Welcoming Haven

DeborahRating, 5 stars1 week ago

Patricia's place is a great hideaway with easy access to some of the areas highlights, including Shelburne Falls and Mass MOCA (within 40 minutes). The space is thoughtfully decorated, the kitchen is extremely well-stocked and her warm welcome of our dog was much appreciated. With or without a canine companion, this is a terrific, quiet spot. Highly recommend.

The kitchen features modern white cabinetry and a spacious island with seating for two. Intricate blue tile backsplash adds a decorative touch. Natural light fills the area through multiple windows, highlighting the wide plank hardwood floors and elegant pendant lighting.

Home in Stonington

4.98 out of 5 average rating, 171 reviews

Historic charm & modern luxury in downtown Mystic

RacelRating, 5 stars1 week ago

My family of 6 had an awesome stay at K.J.’s place. It was super kid-friendly with lots of books, games, outdoor play spaces, and toys to entertain my two toddlers. It was in an awesome location just a quick and easy walk to downtown Mystic. We were able to easily go into town everyday for lunch and dinner. On top of that, the house was spotless. The beds and linens were super comfortable. And, our hosts were super friendly and responsive. It is just a wonderful place to stay. We felt right at home and would stay again next time we are in town.

Vacation rentals for every style

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Houses

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Apartments

Convenient locations with everyday essentials

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Springfield places to stay

Laptop-friendly workspace

Stay near Springfield's top sights

Baystate Medical Ctr station4 locals recommend

Fletcher's Brooklyn Barbecue28 locals recommend

Stop & Shop27 locals recommend

Red Rose Pizzeria8 locals recommend

MassMutual Center10 locals recommend

Springfield Armory National Historic Site9 locals recommend

Other great vacation rentals in Springfield

Top guest favorite

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

4.93 out of 5 average rating, 319 reviews

Charming Guest Cottage with Modern Amenities

CarolineRating, 5 stars4 months ago

John’s place was the perfect respite for our multi-day stay! The clean and cozy space is perfectly situated close to trails and parks for our Australian shepherd, but only a short drive to all the shopping you’d need (e. g. ShopRite for groceries and necessities). We thoroughly enjoyed our stay and know you will too!

Apartment in Chester

4.77 out of 5 average rating, 197 reviews

Quiet getaway in the Berkshires

MarkRating, 5 stars2 weeks ago

The place is a large upstairs apartment built into a single family home with a business on the first floor. Very Chester. Comfortable and warm. Everything was and felt clean, no worries there.

A snowy slope is visible, surrounded by trees and reflecting bright blue skies. The landscape showcases a gently sloping hill, leading down to a winter scenery filled with scattered homes and dense forest areas in the distance.

4.92 out of 5 average rating, 153 reviews

The Pinnacle House at Otis Ridge Ski Area!

AmyRating, 5 stars2 months ago

Welcoming, tidy and clean home. Fully functional and amenable to families with young children. A perfect winter getaway spot given its proximity to Otis Ridge. Extremely easy to ski in and ski out. Mary Kay is a lovely host- extremely responsive, helpful and flexible.

Top guest favorite

Home in Great Barrington

5 out of 5 average rating, 13 reviews

Great Barrington Ranch. Sleeps 10,Hot Tub, 5 acres

JuanRating, 5 stars1 month ago

We loved this airbnb! The location was perfect very close to Catamount where we went skiing. The house had plenty of space for 9 people. The best part was the host though. Alyssa’s communication is great and she was very flexible and helpful. Would definitely stay again!

Top guest favorite

A modern kitchen features white cabinetry and stainless steel appliances, including an oven and microwave. A teal kettle sits on the stove. Open shelves display kitchen items. The adjacent living area is visible, filled with natural light and cozy seating.

Home in Great Barrington

5 out of 5 average rating, 6 reviews

Summer & Leaf Season Rental!

AnnieRating, 5 stars4 months ago

What a lovely home! It’s in the residential neighborhood above Great Barrington, which means it’s walkable to Lake Mansfield and the trails there and also either a short drive or a nice walk to everything downtown GB has to offer. The house is squeaky clean with nice kitchen amenities, a yard, and a beautiful detached screen porch for warmer months. Perfect size for a small family and very cozy. We will be back!

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

4.85 out of 5 average rating, 310 reviews

In style row house with private hot tub/pool table

MarkRating, 5 stars3 months ago

Great spot - close to the little downtown area with a few restaurants and bars. Lots of room and Ginny was very responsive and clear in her communications. Would definitely stay here again.

4.89 out of 5 average rating, 9 reviews

Family Friendly Mystic Retreat - Close To Town

AlyssaRating, 5 stars5 days ago

Cory was a great host! So responsive and accommodating! The space was beautiful and we had an amazing time for our quick visit to Mystic!

Top guest favorite

Home in Bloomfield

4.96 out of 5 average rating, 118 reviews

Spacious Charming New England Cape

JesseRating, 5 stars2 weeks ago

This is the second time time we've stayed at Carol's place. It's spacious, comfortable, with plenty of open rooms. The kitchen is extremely well stocked. This is becoming our yearly must-stay place!

Quick stats about vacation rentals in Springfield

Total rentals
240 properties
Total number of reviews
9.8K reviews
Family-friendly rentals
90 properties are a good fit for families
Pet-friendly rentals
70 properties allow pets
Rentals with dedicated workspaces
130 properties have a dedicated workspace
Wifi availability
230 properties include access to wifi

Frequently Asked Questions

Where should I stay in Springfield?
Make yourself at home in Springfield by choosing from our most frequently booked neighborhoods. We have over 230 vacation rentals in Indian Orchard, over 50 vacation rentals in Boston Road, and over 10 vacation rentals in Suffield Corner.
How much does it cost to stay in bed and breakfast rentals in Springfield?
Experience the best of Springfield with our bed and breakfast rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there house rentals with a dedicated workspace in Springfield?
Yes! Work meets play with ease at over 80 house rentals in Springfield featuring dedicated workspaces. Stay connected and productive in your home away from home.
What are the most popular amenities for House Rentals in Springfield?
Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with self check-in, over 140 homes with wifi, over 10 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there pet-friendly apartment rentals in Springfield?
Four-legged friends are welcome in Springfield. Choose from more than 10 apartment rentals for guests traveling with pets.
Do apartment rentals in Springfield have self check-in?
Absolutely! We offer over 10 apartment rentals with self check-in in Springfield. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Springfield have a bbq area?
Absolutely! We offer over 10 house rentals with a bbq area in Springfield. Enjoy a tailored experience with all the comforts you desire.
Do bed and breakfast rentals in Springfield have wifi?
Absolutely! We offer over 10 bed and breakfast rentals with wifi in Springfield. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore