Southampton Holiday Rentals from €255: Search Short-Term Rentals

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

Experience Three Sisters Sanctuary in Goshen, MA : This holiday home rental outside of Southampton is equipped with a garden, air conditioning and a Smart TV to help you feel comfortable during your stay.

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Southampton holiday rentals

A hot tub on a wooden deck with snow on the ground and trees in the background.

1. The Creation Station is a cozy place so make yourself at home.

Easthampton Ma.

Paula

includes taxes & fees

18 Nov - 19 Nov

A two-story house with a front porch, a sign reading "Victory Residence," and the address "1785."

2. Modern Studio Ideal for Traveling Professionals

Holyoke

Kebreab H.

includes taxes & fees

16 Nov - 17 Nov

A two-story residential building with a sign indicating 'Victory Residence' and the address '1785'.

3. Work, Play & Stay! Apt Near Holyoke Medical Center

Holyoke

Yvonne A.

includes taxes & fees

22 Nov - 23 Nov

4. Modern Studio Ideal for Traveling Professionals

Holyoke

includes taxes & fees

16 Nov - 17 Nov

A two-story house with a front porch, a concrete walkway, and a well-maintained lawn.

5. Cozy Home in Holyoke with 3 bedrooms

Holyoke

Jennifer S.

includes taxes & fees

27 Nov - 28 Nov

A living room with a fireplace, a sofa, a coffee table, and a TV.

6. Cozy 2-bedroom apartment in Chicopee

Chicopee

Christopher P.

includes taxes & fees

17 Nov - 18 Nov

A modern kitchen with a central island, bar stools, and a bicycle.

7. Button's Modern Luxury Walkup Downtown Northampton

Northampton

AMY

A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a pool table.

8. Townhouse with Pool Table - Renovated w/ King Bed

Chicopee

Nicholas B.

includes taxes & fees

16 Nov - 17 Nov

A living room with a sofa set, a coffee table, and two lamps.

9. Cozy First Floor Apartment. Located in a quiet neighborhood.

Chicopee

Morrris

includes taxes & fees

29 Nov - 30 Nov

A modern reception area with a counter, two chairs, a small table, and a carpeted floor.

10. 1 King Bed|Smoking, Micfridge

Enfield

includes taxes & fees

16 Nov - 17 Nov

A single-story house with a red front door, white siding, and a brick chimney.

11. Red Door Retreat West Springfield 3 bedroom w/ Game Room! Near Big E & Six Flags

West Springfield

"Adorable home, set up so cute plus being pet friendly means everything to me when deciding. All was as described and our host had everything you could need and more available to us in the well stocked kitchen and bathroom. Very quiet safe and friendly neighborhood on a dead end street, gated walkway as well as a gated driveway made me feel plenty safe enough to take my dog out at night. Bedrooms were welcoming and set up with pretty fairy lights throughout, all three beds were very comfortable...

Jaimie F.

includes taxes & fees

16 Nov - 17 Nov

A white porch with two rocking chairs, a door, and a number '205'.

12. Big farmhouse in the foothills of the Berkshires

Russell

Dale B.

includes taxes & fees

16 Nov - 17 Nov

A television displaying a coastal scene, a window with a view of buildings, and a sign reading 'CAPE COD'.

13. Penthouse overlooking downtown Amherst!

Amherst

Mike S.

includes taxes & fees

16 Nov - 17 Nov

A modern fireplace with a glass enclosure, decorative items, and a sign that reads 'blessed.'

14. A Scenic Townhouse Near Amherst (Next to a Horse Farm)

Sunderland

Sherry T.

A gazebo with seating, surrounded by a fenced area with trees and a clear sky.

15. Serene 1-bedroom suite on 75 acre horse property

Belchertown

Anna O.

A square fire pit with flames, surrounded by a grassy field and a green chair.

16. Peaceful Meadow Retreat

Granby

Todd R.

A modern living room with a flat-screen TV, a wooden coffee table, a gray sofa, a patterned rug, and a staircase with wooden steps.

17. Modern 3BR Duplex - Sleeps 6 - Off-Street Parking

East Springfield

Tami G.

includes taxes & fees

29 Nov - 30 Nov

A spacious living room with a wooden staircase, a dining area, and a television.

18. Real Estate: Therapy - Lake, Laundry, Love it

Sherwood Forest

William C B.

includes taxes & fees

26 Nov - 27 Nov

A modern kitchen with a marble island, bar stools, a stainless steel stove, and a decorative chandelier.

19. Cozy 2-bedroom apartment with movie theater.

Agawam

Eric R.

includes taxes & fees

16 Nov - 17 Nov

A modern kitchen with white cabinetry, stainless steel appliances, and a wooden floor.

20. Bling nest

Ludlow

includes taxes & fees

16 Nov - 17 Nov

View all properties

Find holiday rentals that suit your style

Apartments

Cabins

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Southampton Hotel Reviews

D. Hotel Suites & Spa

10/10 Excellent

"Always friendly, always clean and comfortable. Our go-to in the Holyoke area."

Find out more about Southampton

Everything you need to know about Southampton holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Southampton holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Southampton holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Southampton holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Southampton. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Southampton holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Southampton holiday rentals we have selected for you start as low as €255 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Southampton rentals

At Expedia, we put the best Southampton holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Southampton rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Southampton holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Southampton. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Are there holiday rentals in Southampton?

Yes, there are holiday rentals close to the most popular sights in Southampton, or you can select a more secluded option if you're looking for a relaxing stay. Southampton is known for its restaurants and shopping.

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

Experience Three Sisters Sanctuary in Goshen, MA: This holiday home rental outside of Southampton is equipped with a garden, air conditioning and a Smart TV to help you feel comfortable during your stay.

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.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Southampton holiday rentals

1. The Creation Station is a cozy place so make yourself at home.

2. Modern Studio Ideal for Traveling Professionals

3. Work, Play & Stay! Apt Near Holyoke Medical Center