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Southampton Holiday Rentals

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Holiday Rentals in Southampton

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

9.0 out of 10, Wonderful, (6)
"Great property! Thank you for a wonderful stay."
The price is AU$577
includes taxes & fees
11 Aug - 12 Aug
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!

Charming Chicopee Getaway

The price is AU$526
includes taxes & fees
2 Aug - 3 Aug
Charming Chicopee Getaway

Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

9.6 out of 10, Exceptional, (31)
"Very clean, good host, well stocked kitchen, good location in Springfield, good beds and bathrooms, quiet. Living room and dining room have very unusual dramatic red furniture and a throne chair, but we enjoyed the eccentric touch. "
The price is AU$506
includes taxes & fees
31 July - 1 Aug
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

PICON COZY

7.4 out of 10, Good, (68)
"This home has the basics and is reasonably comfortable. The parking is good and the area is walkable. It was adequate for my needs. "
The price is AU$245
includes taxes & fees
28 July - 29 July
PICON COZY

Bring Your Pet & Visit Springfield: Westfield Home

2.0 star property
6.0 out of 10, (11)
"The house and location were perfect. Comfortable beds! Would definitely stay again"
Bring Your Pet & Visit Springfield: Westfield Home

Easthampton Vacation Rental - Walk to Breweries!

9.6 out of 10, Exceptional, (20)
"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! "
The price is AU$368
includes taxes & fees
29 July - 30 July
Easthampton Vacation Rental - Walk to Breweries!

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

9.6 out of 10, Exceptional, (42)
"We had a wonderful stay. The cabin was clean and comfortable! "
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

comfort, luxury, privacy

9.8 out of 10, Exceptional, (64)
"Clean and comfortable property! Perfect for visiting the Amherst area. It was easy to get to the Dickinson House and the Eric Carle Museum. Would definitely stay again. "
comfort, luxury, privacy

Spacious 4-bedroom condo with AC and WiFi in charming Enfield

10.0 out of 10, Exceptional, (1)
"I had a family event in the area and needed a place for 8 people that was of better value than hotel rooms. This location was the perfect option."
The price is AU$817
includes taxes & fees
28 July - 29 July
Spacious 4-bedroom condo with AC and WiFi in charming Enfield

LAKE FRONT ISLAND HIDE-AWAY WITH BOAT DOCK

9.8 out of 10, Exceptional, (9)
"Beautiful lake, traditional charming cottage- great get-away"
LAKE FRONT ISLAND HIDE-AWAY WITH BOAT DOCK

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (138)
"It is a quiet and beautiful home. The surrounding nature is peaceful and we saw many kinds of birds."
The price is AU$560
includes taxes & fees
28 July - 29 July
Big farmhouse in the foothills of the Berkshires

HOMEY HOMEY

3.4 out of 10, (3)
"We checked out early. The place had mold/mildew. Power went out and the place was dark. Not suitable for human use without major renovations and updates."
The price is AU$257
includes taxes & fees
28 July - 29 July
HOMEY HOMEY

Newly Built Barn Loft in Pioneer Valley

2.0 star property
9.4 out of 10, Exceptional, (14)
"This was a sweet place to stay while we were in the area for a graduation. It is a beautiful little apartment with everything we needed, cozy and quiet, and Lucienne’s communications were clear and welcoming!"
The price is AU$325
includes taxes & fees
28 July - 29 July
Newly Built Barn Loft in Pioneer Valley

Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft

9.6 out of 10, Exceptional, (36)
"My wife and I had a wonderful and relaxing time celebrating our anniversary. We really enjoyed sitting by the river."
Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft

Button's Modern Luxury Walkup Downtown Northampton

The price is AU$764
includes taxes & fees
3 Aug - 4 Aug
Button's Modern Luxury Walkup Downtown Northampton

5 bedroom in the center of Springfield .

9.0 out of 10, Wonderful, (8)
"As advertised, great communication, would stay there again!"
5 bedroom in the center of Springfield .

Amherst, Perfect Location, UMass, Smith, MHC!

10.0 out of 10, Exceptional, (16)
"House was great, very comfortable, location was perfect for our needs. All of us had an excellent stay."
Amherst, Perfect Location, UMass, Smith, MHC!

Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath. Sleeps 7.

9.6 out of 10, Exceptional, (60)
"Great"
Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath. Sleeps 7.

Privacy, entertainment, comfort galore 2 BR LR 1BA Home Theater, Pool Table

10.0 out of 10, Exceptional, (68)
"From booking through check out everything about our experience was amazing! The host was very responsive and helpful with any questions I had. The space was very clean and the host had thought of everything guests could need. We will definitely book again when we travel to the area!"
Privacy, entertainment, comfort galore 2 BR LR 1BA Home Theater, Pool Table

The Clearing - Quiet - Close To Nature

10.0 out of 10, Exceptional, (192)
"Wonderful getaway, lovely hosts, great location, overall a fabulous place to relax and recharge. "
The Clearing - Quiet - Close To Nature
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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Top Southampton Hotel Reviews

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?

Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!: This holiday home rental outside of Southampton is located in the mountains, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

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. Edwards Public Library 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.