Photo by Heather Beaudry

Holiday Rentals in Southampton

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Holiday Rentals in Southampton

comfort, luxury, privacy

9.8 out of 10, Exceptional, (58)
"Our stay was great. The space was comfortable and cozy. Was nice to have a kitchen to cook a little and they included fresh eggs with other snacks to make it welcoming. "
The price is €181
includes taxes & fees
10 Apr - 11 Apr
comfort, luxury, privacy

Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!

The price is €422
includes taxes & fees
6 Apr - 7 Apr
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!

The Clearing - Quiet - Close To Nature

10.0 out of 10, Exceptional, (187)
"Thank you for sharing your wonderful home! It had everything we needed including a quiet, peaceful, private, beautiful location, comfortable bed, great books!!, and a well equipped kitchen. We are very grateful you had availability for our Thanksgiving visit with family. Thank you!!"
The Clearing - Quiet - Close To Nature

PICON COZY

7.8 out of 10, Good, (61)
"Peaceful everything just as listed "
The price is €158
includes taxes & fees
13 Apr - 14 Apr
PICON COZY

Home in the woods

9.4 out of 10, Exceptional, (22)
"Then property is very spacious and is in a rustic setting. It was ideal for us as we had Christmas there with our family. "
Home in the woods

Chic Downtown Retreat Furnished 2-Bedroom with Trail Access & Outdoor Oasis

5.0 out of 10, (2)
"Perfect location and good place to stay!"
Chic Downtown Retreat Furnished 2-Bedroom with Trail Access & Outdoor Oasis

Easthampton Apartment Near Breweries & Rail Trail!

9.6 out of 10, Exceptional, (10)
"This was a super nice stay: great location to attend the Back Porch Music Fest. Easy drive to Tree House Brewery in Deerfield. Property was very nice, clean, had ammenities for a great stay. Host was extremely helpful to me. I highly recommend!"
Easthampton Apartment Near Breweries & Rail Trail!

Bring Your Pet & Visit Springfield: Westfield Home

2.0 star property
6.6 out of 10, (4)
"The house and location were perfect. Comfortable beds! Would definitely stay again"
Bring Your Pet & Visit Springfield: Westfield Home

Hilltown Nest is a wonderful place for family and friends to gather.

9.8 out of 10, Exceptional, (15)
"Sadly we were only here for a couple of nights, but this place was very nice. I manage vacation rentals myself and i was very impressed by the cleanliness of this place, especially considering the size of it. The house is great for a family with lots of room to spread out. Our grandkids enjoyed tinkling on the piano and playing in the backyard. Would definitely choose to stay here again!"
Hilltown Nest is a wonderful place for family and friends to gather.

Author Stephen Oates Once Owned

8.0 out of 10, Very good, (1)
"The house is very close to Amherst on a quiet street. Plenty of room, comfortable beds, and well supplied. We’d stay again! "
The price is €378
includes taxes & fees
7 Apr - 8 Apr
Author Stephen Oates Once Owned

The Meadows House @ Otis Ridge w/ 7-person hot tub

9.8 out of 10, Exceptional, (28)
"perfect size for group of 7 adults...Good location especially for snow shoeing....cross country sking...enjoyed being in berkshires..."
The Meadows House @ Otis Ridge w/ 7-person hot tub

Trainmaster's Inn - Caboose

9.6 out of 10, Exceptional, (4)
"We felt right at home the minute we walked thru the door! Its the most unique place we have ever stayed. The caboose had so many of the original feature. The Innkeepers are readily available and very kind.The outside fire pit area was enjoyed nightly. "
The price is €295
includes taxes & fees
14 Apr - 15 Apr
Trainmaster's Inn - Caboose

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (130)
"Cozy, historic experience from great owners. Nice trail and brook right behind the house as well. "
The price is €340
includes taxes & fees
6 Apr - 7 Apr
Big farmhouse in the foothills of the Berkshires

Charming 4Bds+1crib house with patio Amherst Center

2.0 star property
10.0 out of 10, Exceptional, (2)
"A great place for a family stay in downtown Amherst. "
The price is €426
includes taxes & fees
7 Apr - 8 Apr
Charming 4Bds+1crib house with patio Amherst Center

Thomas's Cozy Duplex - Centrally Located

8.6 out of 10, Excellent, (10)
"The duplex was clean and quiet. The kitchen was stocked well enough for us to make dinner, although there was no kitchen towel for drying hands and dishes (very minor). Three bedrooms, two with a double/queen, one with a single, and it looked like the couch in the living room was a pull out. Beds were comfortable with plenty of bedding. Wi-fi worked well. Couldn't ask for anything more. I would stay here again if in the area. "
Thomas's Cozy Duplex - Centrally Located

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.6 out of 10, Exceptional, (39)
"A nice cabin in the woods. Only issue was rodents at the property. We had four sighting in three days. Would stay again if they resolved the mouse problem."
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

Peace and quiet on the lake

9.6 out of 10, Exceptional, (212)
"This property was in an incredible location with a nice cozy feel. It was perfect for my family of 6. I highly recommend this place!"
Peace and quiet on the lake

Spacious Private Retreat Near Holyoke State Park!

10.0 out of 10, Exceptional, (7)
"It was a quite place to relax. No noise from traffic or people. Short drive to activites to do with family "
Spacious Private Retreat Near Holyoke State Park!

Pristine Home In Becket Woods

10.0 out of 10, Exceptional, (14)
"Pristine can mean several different things. My interpretation was to be “like new”. This dwelling did not quite live up to that standard, but was clean, sans the “mud room” and what appeared to be mold on the peak of the ceiling above the living room. The original listing stated firewood was provided by the host. Then, the checkin instructions stated guests provided their own. Not huge, just misstated in the listing (since changed). There was a power outage while we were there, thus no...
Pristine Home In Becket Woods

Easthampton Vacation Rental - Walk to Breweries!

9.6 out of 10, Exceptional, (10)
"Our group had a wonderful time and we will not hesitate to book again in the future. The place was exceptionally clean, well appointed, and very comfortable. Overall it was a great experience! "
Easthampton Vacation Rental - Walk to Breweries!
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.
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Other types of properties in Southampton you may be interested in

MGM Springfield

4.0 star property
8.8 out of 10, Excellent, (1337)
"The room was very clean and nice, many food options, and the casino was great. Enjoyed our stay a lot."
The price is €194
includes taxes & fees
8 Apr - 9 Apr
MGM Springfield

Howard Johnson by Wyndham Amherst Hadley

2.0 star property
7.2 out of 10, Good, (1000)
"Was kind of nervous since the outside of the hotel looked sketchy and old however it was surprisingly decent. The free breakfast was delicious, the staff was nice and helpful, the room was clean. Will definitely stay here again next time I’m in the area. "
The price is €101
includes taxes & fees
7 Apr - 8 Apr
Howard Johnson by Wyndham Amherst Hadley

D. Hotel Suites & Spa

3.0 star property
9.4 out of 10, Exceptional, (2325)
"Beautiful hotel with excellent service. "
The price is €128
includes taxes & fees
8 Apr - 9 Apr
D. Hotel Suites & Spa
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.

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?

Remote and Relaxing Cabin in the Berkshires: This holiday home rental outside of Southampton is located near skiing, and has a patio, a selection of games and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What can I see and do in Southampton?

Conant Park and Southampton Center Historic District are a couple of lovely local spots to get outside and enjoy nature. Southampton Wildlife Management Area and Southampton Town Hall are other places to visit while you're in town.

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.