
House holiday rentals in Springfield
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Top-rated house rentals in Springfield
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Popular amenities for house rentals in Springfield
House rentals with a pool

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

The 1770 House
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!

The Getaway-HOST & Co.
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.

Pool House
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.

Garden Level Suite with Beautiful Pool
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!

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

Private apartment
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

Hot Tub~Pool~Game Room~Fire Pit~BBQ~Casinos
We had a great stay at this property! Andrew was very communicative and the house was as-advertised.
Weekly house rentals

Stockbridge Cape Near Tanglewood!
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.

Lake Front Family Oasis
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.

Litchfield County Getaway
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

5•Star CapeCodStyle Gem with Bedroom on the Main
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!

Former Sunset View Inn
Fabulous location that had everything we needed! Fantastic place for a group getaway weekend!

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

Explore Holyoke from this charming 3 Bedroom house
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.

A Mini Palace w/ 5 Queen @ Mystic Seaport
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

The Berkshires Mountain Terrace LUX Home Sleeps 7
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.

Stunning Artisan Waterfall Escape, Walk Downtown
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.

Moonstone Lake House – romance and serenity
My husband and I had a great weekend at Mighty's home. Everything was clean and the house was very homey and comfortable.

Peaceful Berkshire Getaway (A/C, Lake Access)
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!

Lovely House
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.

Luxury/pool/private Villa Mariana Blackberry River
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.

Central Haus (Group getaway on a quiet street)
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.

Spacious, private home, must see!
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
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