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Southampton Holiday Rentals

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Check prices for these dates

In two weeks
19 Sept - 21 Sept
In two months
31 Oct - 2 Nov
In three months
28 Nov - 30 Nov
In four months
26 Dec - 28 Dec

Holiday Rentals in Southampton

Tiny Home with AC and WiFi in lovely Ludlow
1 bedroom, WiFi, bed sheets

Tiny Home with AC and WiFi in lovely Ludlow

9.0 out of 10, Wonderful, (6)
The price is HK$616
HK$1,167 total
includes taxes & fees
8 Sept - 9 Sept
Tiny Home with AC and WiFi in lovely Ludlow
5 bedroom in the center of Springfield .
Interior

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 .
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Exterior

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

9.6 out of 10, Exceptional, (221)
"Cabin was exactly what we were looking for in a weekend away. Great location, quiet, and had everything we needed. Hope to go back again soon! "
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Old World Charm, Modern Conveniences - 3 BR private home in quiet setting
Fridge, microwave, oven, stovetop

Old World Charm, Modern Conveniences - 3 BR private home in quiet setting

10.0 out of 10, Exceptional, (21)
"This beautiful home was perfect for our short stay in Western Massachusetts. Everything was just lovely, clean, comfortable, quiet. Great hosts and so kind and accommodating to our needs. Thank you so much. We will definitely look to stay here again for future family visits. "
Old World Charm, Modern Conveniences - 3 BR private home in quiet setting
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
Smart TV, fireplace, video games, books

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

9.6 out of 10, Exceptional, (34)
"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 HK$1,560
HK$2,619 total
includes taxes & fees
30 Sept - 1 Oct
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
Charming Chicopee Getaway
Fridge, microwave, oven, stovetop

Charming Chicopee Getaway

10.0 out of 10, Exceptional, (1)
"We really appreciated the stay to get together with family. There was plenty of space to play with the toddler and set up the pack-n-play for the infant. And then plenty of room to play board games after the babies were put to bed. "
The price is HK$624
HK$1,955 total
includes taxes & fees
8 Sept - 9 Sept
Charming Chicopee Getaway
Stunning 3BR Riverfront Log Home with Soaring Glass Wall & Private Forest
Fireplace, books

Stunning 3BR Riverfront Log Home with Soaring Glass Wall & Private Forest

9.6 out of 10, Exceptional, (37)
"My wife and I had a wonderful and relaxing time celebrating our anniversary. We really enjoyed sitting by the river."
Stunning 3BR Riverfront Log Home with Soaring Glass Wall & Private Forest
LAKE FRONT ISLAND HIDE-AWAY WITH BOAT DOCK
Property grounds

LAKE FRONT ISLAND HIDE-AWAY WITH BOAT DOCK

10.0 out of 10, Exceptional, (14)
"Beautiful lake, traditional charming cottage- great get-away"
LAKE FRONT ISLAND HIDE-AWAY WITH BOAT DOCK
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
Fridge, microwave, oven, stovetop

Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield

9.0 out of 10, Wonderful, (11)
"I was in a nice, quiet neighborhood. House was clean and comfy. There is a store literally right around the corner. I would definitely stay agin and recommend to others. The property manager answered my questions and gave good customer service."
The price is HK$1,092
HK$2,645 total
includes taxes & fees
8 Sept - 9 Sept
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!
Fridge, microwave, oven, stovetop

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

9.2 out of 10, Wonderful, (13)
"Great property! Thank you for a wonderful stay."
The price is HK$1,053
HK$2,439 total
includes taxes & fees
9 Sept - 10 Sept
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!
3-bedroom house in perfect Springfield with WiFi, AC
TV

3-bedroom house in perfect Springfield with WiFi, AC

2.0 star property
9.2 out of 10, Wonderful, (5)
3-bedroom house in perfect Springfield with WiFi, AC
The Clearing - Quiet - Close To Nature
Outdoor pool

The Clearing - Quiet - Close To Nature

10.0 out of 10, Exceptional, (198)
"The property was beautiful and well maintained.The home where we stayed was perfect and cozy."
The Clearing - Quiet - Close To Nature
Newly Built Barn Loft in Pioneer Valley
Smart TV, books, stereo

Newly Built Barn Loft in Pioneer Valley

2.0 star property
9.4 out of 10, Exceptional, (15)
"Small but well maintained, clean, well stocked & nic"
The price is HK$1,228
HK$1,653 total
includes taxes & fees
8 Sept - 9 Sept
Newly Built Barn Loft in Pioneer Valley
HOMEY HOMEY

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 HK$561
HK$1,300 total
includes taxes & fees
8 Sept - 9 Sept
HOMEY HOMEY
Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!
Fridge, microwave, oven, stovetop

Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!

9.0 out of 10, Wonderful, (23)
"Check in was easy. This met all of our needs. "
The price is HK$3,111
HK$5,547 total
includes taxes & fees
1 Oct - 2 Oct
Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!
Spacious 4-bedroom condo with AC and WiFi in charming Enfield
Microwave, oven, stovetop

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 HK$975
HK$3,234 total
includes taxes & fees
8 Sept - 9 Sept
Spacious 4-bedroom condo with AC and WiFi in charming Enfield
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
Terrace/patio

kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

9.8 out of 10, Exceptional, (107)
"My wife and I stayed in the upper apartment for 2 nights. The place was perfect in every aspect. It was clean, quiet and well equipped. Beds were comfortable and it was close the UMASS. We will definitely stay here again when we are in the area. "
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath. Sleeps 7.
Terrace/patio

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

9.6 out of 10, Exceptional, (62)
"Great"
Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath. Sleeps 7.
Big farmhouse in the foothills of the Berkshires
Property grounds

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (139)
"Lovely old farmhouse with authentic yet comfortable furnishings. Would recommend!"
The price is HK$1,560
HK$2,794 total
includes taxes & fees
8 Sept - 9 Sept
Big farmhouse in the foothills of the Berkshires
Newly Renovated 4 Bedroom House
Fridge, microwave, stovetop, dishwasher

Newly Renovated 4 Bedroom House

10.0 out of 10, Exceptional, (2)
"The house was perfect for a weekend wedding trip. "
Newly Renovated 4 Bedroom House
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

Find out more about Southampton

Find out more about Southampton

Search for holiday rentals in Southampton on Expedia! You can easily find your home rentals, villas, holiday apartments in Southampton using one of the methods below:

  • View our selection of featured holiday rentals in Southampton
  • Use the map to find apartments and other holiday homes in the Southampton neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Southampton while they last

Look no further and take a look at our great range of rental properties in Southampton!

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?

Tiny Home with AC and WiFi in lovely Ludlow: This holiday home rental outside of Southampton has air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings.

What can I see and do in Southampton?

Conant Park and Pulaski Park are a couple of lovely local spots to get outside and enjoy nature. Southampton Town Hall and Edwards Public Library 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.