House holiday rentals in Springfield

Find and book unique houses on Airbnb

When results are available, navigate with the up and down arrow keys or explore by touch or swipe gestures.
0 of 0 items showing
1 of 3 pages

Popular amenities for house rentals in Springfield

House rentals with a pool

Guest favourite
Home in Woodbury
4.94 out of 5 average rating, 18 reviews

2 homes in one (in-law design) w/salt water pool

ChristineRating, 5 stars5 months ago
Julie is an outstanding host! This house is perfect for any getaway. It was clean, spacious, well equipped, comfortable, and STUNNING outdoor area with a gorgeous pool. This is 3 FULL baths and 1/2 bath!! Two kitchens! Two family rooms! You had space! It made you want to relax! The kitchen was well stocked with any utensil or appliance you would need. It was private. You could really escape and get away. Woodbury and the surrounding towns were jampacked with things to do. There were many places to choose from to eat. Such a variety from steak, seafood, pizza, and American fare pubs and other specialty restaurants. Lots of variety/antique shops, flea market, wine/liquor stores, convenience stores. Just a short drive into Southbury you find more shops, antiques, restaurants, bigger, grocery store, etc. We also drove to a few other neighboring towns. All under 45 minutes. Friendly people! We had a wonderful time! Price is fabulous, house/outdoor area is A+ value! Thank you Julie!!
Guest favourite
Home in Colrain
4.9 out of 5 average rating, 126 reviews

The 1770 House

BrianRating, 5 stars1 month ago
Another great weekend at Ed’s! It was our group’s second time staying here, and we loved it just as much as the first, which is to say—a lot! Ed is very considerate and responsive, and there’s plenty to do for everyone. We are already looking forward to next year!
Superhost
Home in Litchfield
4.82 out of 5 average rating, 105 reviews

The Getaway-HOST & Co.

CrystalRating, 5 stars6 months ago
I absolutely enjoyed my weekend here. The home is beautiful. Everything you could possibly need was provided In the home. Everything was clean, and neat. House is filled with light. The pool and hot tub were enjoyable. The host were amazing and had great communication, assisted us when needed right away. I would highly recommend staying here, and they are pet friendly which is always a plus for me. The yard is fenced in. Which made it easy to let the dog out, and great for the dog to explore. A++++ Will probably be back sometime In the future.
Top guest favourite
Home in Cheshire
5 out of 5 average rating, 131 reviews

Pool House

MelissaRating, 5 stars2 months ago
This was our second time back to the pool house and it was amazing, again. We thinks of everything to make you feel welcome. Milk and eggs in the fridge. Muffins and croissants waiting for you. Pristine home. Fully stocked kitchen. I was even able to host a few family members for Christmas dinner and had everything I needed to make a lovely dinner. We also travel with two dogs and Sue is so accommodating, making our pups feel right at home. Thank you, Sue, for making our holidays away from home so peaceful and enjoyable.
Top guest favourite
Home in Monroe
4.97 out of 5 average rating, 200 reviews

Garden Level Suite with Beautiful Pool

GraceRating, 5 stars2 weeks ago
We had an amazing time at Marybeth’s suite—it truly felt like a winter wonderland. Our kids had a blast "swimming" in the snow and "rolling" over the gentle hills. Every moment was filled with joy, whether we were relaxing in the sunroom, playing in the snow, or swinging outside. The time spent together as a family, along with our conversations with Marybeth and her family, was truly precious. We can’t wait to return in the summer!
Guest favourite
Home in Litchfield
4.99 out of 5 average rating, 84 reviews

Hilltop House w/POOL/SPA- HOST & Co.

DanielRating, 5 stars3 weeks ago
Great house and great host. The place was beautiful -- big kitchen, comfortable bedrooms, great bathrooms (especially in the master bedroom), nice setup outside (jacuzzi and BBQ), etc. Perfect place for a family weekend in Litchfield. Location was perfect -- a 2 minute drive to great coffee, pastries, bread, ice cream, etc. in Bantam. Liz was an excellent host -- very helpful and responsive. We'd love to visit again soon.
Superhost
Home in Danbury
4.85 out of 5 average rating, 113 reviews

Private apartment

CarineRating, 5 stars1 month ago
This was my second time saying at this location. It is always clean and exactly as described getting to the actual apartment is a bit tricky but well worth it for the price and wonderful hosting. I absolutely recommend staying here. It is a great little getaway or a perfect spot to stay for your business trip
Top guest favourite
Home in Montville
4.96 out of 5 average rating, 139 reviews

Hot Tub~Pool~Game Room~Fire Pit~BBQ~Casinos

MathewRating, 5 stars1 week ago
We had a great stay at this property! Andrew was very communicative and the house was as-advertised.

Weekly house rentals

Top guest favourite
Home in Stockbridge
4.93 out of 5 average rating, 41 reviews

Stockbridge Cape Near Tanglewood!

MarkRating, 5 stars3 months ago
Very nice accommodations in a great location. A vehicle needed to get around to plentiful hiking, shops in nearby towns, and cultural sites. Very nice home for family gatherings and with all necessary amenities.
Top guest favourite
Home in New Fairfield
5 out of 5 average rating, 35 reviews

Lake Front Family Oasis

JasmineRating, 5 stars1 week ago
Stayed here with 8 friends and we enjoyed it so much! Honestly the pictures do not do it justice. The view to the lake was so nice and our favorite part was waking up to that beautiful sunrise view, absolutely stunning! The place is big and roomy and everyone slept so comfortable. House was perfect in such a cute community and it was very clean I would definitely stay here again if I ever come back.
Guest favourite
Home in Warren
4.94 out of 5 average rating, 108 reviews

Litchfield County Getaway

DemianRating, 5 stars3 months ago
Was in the area to visit family and this was a perfect location for me. Had just what my family needed to have a great weekend
Guest favourite
Home in New Britain
4.89 out of 5 average rating, 103 reviews

5•Star CapeCodStyle Gem with Bedroom on the Main

JulieRating, 5 stars2 months ago
I lost count of how many times I had booked Chana's place. My family and I are always satisfied with the hospitality of Chana and team! The place is as described on the listing and is the same as in the pictures. The house is clean and has every basic thing that you need. The host quickly response to our questions. We will definitely book again when we come back!
Guest favourite
Home in Great Barrington
4.94 out of 5 average rating, 114 reviews

Former Sunset View Inn

AutumnRating, 5 stars4 months ago
Fabulous location that had everything we needed! Fantastic place for a group getaway weekend!
Guest favourite
Home in Sturbridge
4.96 out of 5 average rating, 168 reviews

Cedar Lake 3 Bed 3 1/2 Bath Home Sturbridge MA

JillRating, 5 stars4 months ago
This was our second time to stay. It had a gorgeous view surrounded by beautiful trees. It was so peaceful and relaxing with everything we needed. James is so easy to work with and very responsive. Highly recommended!
Top guest favourite
Home in Holyoke
4.97 out of 5 average rating, 323 reviews

Explore Holyoke from this charming 3 Bedroom house

LeahRating, 5 stars2 months ago
Great place to stay! Just as the listing states, it's in Holyoke right across from a lovely park (our kids are teens, but there's a playground right there for the younger set). Very easily accessible to other points in the Pioneer Valley. Joseph is a friendly and responsive host -- he even offered to pick up groceries for us since we were arriving on a holiday! Would stay again when we are in the area.
Guest favourite
Home in Old Mystic
4.9 out of 5 average rating, 147 reviews

A Mini Palace w/ 5 Queen @ Mystic Seaport

GinaRating, 5 stars1 month ago
We enjoyed staying at the place. It is very clean and had an equipped kitchen for our short stay. Charlotte was very helpful with our inquiries. Highly recommend this place.

Private house rentals

Top guest favourite
Home in Egremont
4.96 out of 5 average rating, 120 reviews

The Berkshires Mountain Terrace LUX Home Sleeps 7

CourtneyRating, 5 stars2 weeks ago
This was a beautiful and well kept home and was a delight to stay in. Natalia was also a lovely and communicative host. We had no issues and would happily stay there again.
Guest favourite
Home in Chester
4.98 out of 5 average rating, 209 reviews

Stunning Artisan Waterfall Escape, Walk Downtown

TimRating, 5 stars4 months ago
We'd been looking forward to coming back to The Recycle House since we first stayed there in 2022. Safe to say it was just as we remembered it...great house, great location, wonderful community. Looking forwarded to returning.
Top guest favourite
Home in Belchertown
4.98 out of 5 average rating, 58 reviews

Moonstone Lake House – romance and serenity

ColleenRating, 5 stars1 month ago
My husband and I had a great weekend at Mighty's home. Everything was clean and the house was very homey and comfortable.
Superhost
Home in Canaan
4.96 out of 5 average rating, 72 reviews

Peaceful Berkshire Getaway (A/C, Lake Access)

PaulRating, 5 stars8 months ago
Becky’s house was exactly as listed with plenty of space to relax and enjoy the area. Her gardens are beautiful and the house is convenient to the Berkshires without the stress of the downtown areas. We are extremely appreciative of all that was provided!
Guest favourite
Home in Springfield
4.91 out of 5 average rating, 164 reviews

Lovely House

MattRating, 5 stars1 week ago
We continue to stay at Joel's place every time we come to Springfield. He's a fantastic host and we always feel right at home.
Guest favourite
Home in Canaan
5 out of 5 average rating, 14 reviews

Luxury/pool/private Villa Mariana Blackberry River

WayneRating, 5 stars2 months ago
Great stay at Andrea's house in Canaan. House is very nicely renovated and appointed with plenty of room for a family gathering. Walking distance to restaurants in town, and really enjoyed the firepit. Would definitely stay again.
Superhost
Home in North Adams
4.89 out of 5 average rating, 101 reviews

Central Haus (Group getaway on a quiet street)

GenevieveRating, 5 stars3 weeks ago
Wonderful place to stay!! Was so lovely cooking dinner and the place is very cozy- lots of games. Great price for the amount of space. They shoveled the driveway for us twice which was so nice. Would definitely stay again.
Top guest favourite
Home in Newtown
4.97 out of 5 average rating, 156 reviews

Spacious, private home, must see!

CristinRating, 5 stars2 months ago
Very comfortable home in a lovely part of Sandy Hook. The beds and couches are very comfortable. Cozy pillows, quilts and throws to snuggle in. Huge kitchen that is very well equiped.

Quick stats about house rentals in Springfield

  • Total rentals

    140 properties

  • Total number of reviews

    6K reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Pet-friendly rentals

    40 properties allow pets

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wifi availability

    130 properties include access to wifi

Destinations to explore