Photo by Heather Beaudry

Southampton Holiday Rentals

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Holiday Rentals in Southampton

Interior
Peace and quiet on the lake
9.6 out of 10, Exceptional, (184)
"My husband and I had a very peaceful and relaxing long weekend at this lake house! It was very clean and has everything you need. We spent the majority of our time on the wonderful screened-in porch. The location was great and there was a little store/restaurant only a couple minutes walk up the street that was convenient and the food was really good! Overall, a great place to stay!"
Peace and quiet on the lake
Fridge, microwave, oven, stovetop
Cozy apartment located in quiet Williamsburg
9.8 out of 10, Exceptional, (33)
"It’s such a cute apartment- I really enjoyed my time there. The property manager gave me all the information I needed, they were very clear and concise. I did not communicate much with the property manager because everything was perfectly fine."
The price is NZ$426
per night
29 May - 30 May
Cozy apartment located in quiet Williamsburg
Fridge, microwave, oven, stovetop
PICON COZY
8.0 out of 10, Very good, (43)
"Fidelis demonstrated exceptional professionalism throughout our interaction. He was remarkably accommodating, consistently honest, and promptly addressed any inquiries I had, usually within minutes. On the rare occasion that he couldn't respond immediately, he took the time to provide an explanation and offer his apologies. Recently, my son relocated to this area for work, and thanks to Fidelis, I can now rest assured that my 24-year-old son, who has yet to experience living on his own, is safe...
The price is NZ$279
per night
30 May - 31 May
PICON COZY
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Interior
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
9.8 out of 10, Exceptional, (32)
"We loved our time, very cozy cabin"
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
Microwave, oven, stovetop, dishwasher
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
4.0 out of 10, (1)
"Location has the potential to be great but it is run down and needs A LOT of work. From first walking in, refrigerator was so dirty/dusty you could run your finger down it and have a film on your hand. Wood flooring in kitchen area is warped because of an obvious leak in the ceiling. Ceiling in the kitchen has brown water stains in the ceiling, floor tiles in the upstairs bathroom are cracked, ants kept coming in from outside, food left in the fridge and trash was left in and on the garbage can,...
The price is NZ$379
per night
28 May - 29 May
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
Exterior
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
9.6 out of 10, Exceptional, (195)
"We’ve stayed at the cabin with our dog four times and always enjoy our peaceful stay. It’s cozy, clean and private. Also, the Sherwood Shoppe - just down the road - is a wonderful place for breakfast, homemade chili and much more."
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
2 bedrooms, iron/ironing board, Internet, bed sheets
Easthampton Vacation Rental - Walk to Breweries!
9.4 out of 10, Exceptional, (3)
"This is one of the best properties in the Pioneer Valley for the price. Comfortable, clean, and central. The team at Evolve and the local property manager are incredibly kind and responsive. Check-in was flawless and our stay was an absolute 10/10 from top to bottom. Keep in mind this property does have stairs to get to the bathroom and bedrooms, but the double railings made it a breeze for my elderly parents. The location is unbeatable, so many things to do within a five minute walk from the...
Easthampton Vacation Rental - Walk to Breweries!
Fridge, microwave, oven, stovetop
Spacious three bedroom house near Historic Suffield Center. Pet Friendly!
10.0 out of 10, Exceptional, (2)
"It was wonderful! Enough room for everyone and everything was cozy and working. Appreciate the stay!"
The price is NZ$1,165
per night
29 May - 30 May
Spacious three bedroom house near Historic Suffield Center. Pet Friendly!
Terrace/patio
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
9.8 out of 10, Exceptional, (80)
"Comfortable and convenient"
The price is NZ$342
per night
29 May - 30 May
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
Fridge, microwave, oven, stovetop
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, (7)
"My wife and young daughters live in central CT, and the drive to Becket was both scenic and relatively short at around an hour and a half. The property offers great privacy in a remote wooded setting in the heart of the always beautiful Berkshires. We brought our dog along, and we all were able to relax by the fire, read our favorite books, as well as peruse interesting titles on the impressive bookshelf built into the living room wall—a book lover’s delight. We admired the openness and light...
Pristine Home In Becket Woods
Property grounds
Serene Acreage - Pond - Hiking Trails Nearby
10.0 out of 10, Exceptional, (4)
"Perfect place to relax and have dogs as part of a mini vacation. Very clean, organized, and provided helpful local information. Will definitely stay there again."
Serene Acreage - Pond - Hiking Trails Nearby
Property grounds
Big farmhouse in the foothills of the Berkshires
10.0 out of 10, Exceptional, (120)
"Wonderful place! Thoughtfully decorated, clean and incredibly comfortable. Would rent again."
The price is NZ$594
per night
24 Jun - 25 Jun
Big farmhouse in the foothills of the Berkshires
Fridge, microwave, oven, stovetop
comfort, luxury, privacy
9.8 out of 10, Exceptional, (49)
"The hosts of this property were very responsive even before my arrival, answering questions quickly. The property is easy to access and walking distance from a lovely breakfast spot/market. Their thoughtfulness in leaving snacks for travelers was a lovely touch. It felt like a home away from home -- clean, warm and comfortable!"
comfort, luxury, privacy
Property grounds
The Creation Station is a cozy place so make yourself at home.
10.0 out of 10, Exceptional, (52)
"Wonderful place to stay, had a great time lots of instruments to try, had lots of space to spread out and hangout, the hot tub was very nice and clean. Overall had a fantastic stay the lighted walkway is amazing! All the amenities available where also great, Jon was a great host and we had a great time speaking with him!"
The price is NZ$396
per night
27 May - 28 May
The Creation Station is a cozy place so make yourself at home.
Property grounds
Private Island - Largest Fresh Water Reservoir in Mass....
10.0 out of 10, Exceptional, (3)
"So grateful to Bill for such a wonderful stay! The cottage was so lovely and had everything you could need for a weekend on the lake. Will definitely be returning in the future 😊"
Private Island - Largest Fresh Water Reservoir in Mass....
Property grounds
The Meadows House @ Otis Ridge w/ 7-person hot tub
9.8 out of 10, Exceptional, (20)
"Relaxing get away. Great hot tub, table shuffleboard. 3 floors of comfort."
The Meadows House @ Otis Ridge w/ 7-person hot tub
Exterior
Quintessential 6-BR Berkshires Lodge
10.0 out of 10, Exceptional, (4)
"We had a great time. Place is amazing. Highly recommend. We had four different families and we never felt cramped. Lovely open main room allowed us to stay connected. Bedrooms were nice and spacious, good bed options. Nice decor."
Quintessential 6-BR Berkshires Lodge
Fridge, microwave, oven, stovetop
Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!
9.0 out of 10, Wonderful, (18)
"The property is as advertised. If you have a lot of people that just needs a place to sleep and collect yourseves, this is a wonderful place fir the price. The owner is a pleasure to work with and very responsive. Also met some of the neighbors and it is reassuring that they all watch out for one another."
The price is NZ$951
per night
29 May - 30 May
Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!
Exterior
Secluded Cabin On Acres Of Woods Lake Access
10.0 out of 10, Exceptional, (3)
"Nice cozy cabin close to Otis Ridge Ski mountain - house was clean, comfortable, had everything we needed."
Secluded Cabin On Acres Of Woods Lake Access
Dining
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
9.6 out of 10, Exceptional, (28)
"It was nice stay!"
The price is NZ$513
per night
4 Jun - 5 Jun
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Southampton you may be interested in

8 restaurants, breakfast, lunch, dinner served; American cuisine
MGM Springfield
4.0 star property
8.8 out of 10, Excellent, (1004)
"Really beautiful hotel rooms. Nice pool. Could have more but it’s good for the area. "
The price is NZ$240
per night
27 May - 28 May
MGM Springfield
Exterior
Fairfield Inn & Suites by Marriott Springfield Enfield
2.5 star property
8.8 out of 10, Excellent, (794)
"parking was a problem"
The price is NZ$207
per night
9 Jun - 10 Jun
Fairfield Inn & Suites by Marriott Springfield Enfield
Lobby
Quality Inn West Springfield
2.5 star property
7.2 out of 10, Good, (1002)
"The hotel was clean, quiet and safe. The breakfast was good and accessible. "
The price is NZ$174
per night
4 Jun - 5 Jun
Quality Inn West Springfield
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Southampton holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Southampton. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Southampton. Seeing all the best attractions is bound to make you fall in love with Southampton. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Southampton short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Southampton?

Yes, we offer holiday rentals where you'll be just 14.4 mi (23.1 km) from Six Flags New England, giving you a more remote option if you want a quiet place to stay. Southampton is known for its restaurants and shopping.

What are some of the best holiday rentals that Southampton has to offer?

Cozy apartment located in quiet Williamsburg: This holiday home rental outside of Southampton is in a rural location, and equipped with air conditioning and a Smart TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

What can I see and do in Southampton?

While exploring the area, visit family-friendly sights like Six Flags New England, or get outside and enjoy nature at Smith College Botanic Garden. Holyoke Mall and Volleyball Hall of Fame are a couple of places you'll find in the wider area.

What are holiday rentals like in Southampton?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Southampton. Holiday rentals offer extras such as patios, hot tubs and fire pits so you'll have everything you want. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from shared hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for a small group gathering.

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