Jackson Holiday Rentals

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Holiday Rentals in Jackson

Waterfront cottage with deep water dock, ocean front.

Belfast
9.8 out of 10, Exceptional, (107)
"Truly lovely cottage. Jon is a fantastic host. Highly recommend!"
United States
Peter F.
Waterfront cottage with deep water dock, ocean front.

Cozy Cabin By The Pond, Sleeps 2

Waldo
10.0 out of 10, Exceptional, (197)
"Nice and coat cabin to come back to after long day of beach coming "
United States
Kael G.
The price is AU$282
includes taxes & fees
13 Dec - 14 Dec
Cozy Cabin By The Pond, Sleeps 2

New listing. Charming 3-bedroom lake house in Orrington WiFi, Hot tub, and Sauna

Orrington
10.0 out of 10, Exceptional, (11)
"Wonderful trip and great property!"
United States
Miranda G.
New listing. Charming 3-bedroom lake house in Orrington WiFi, Hot tub, and Sauna

Big Red House - Historic Bangor Home

Bangor
10.0 out of 10, Exceptional, (121)
"We lived our time at the BRH and can’t wait to come back again!"
United States
Emily S.
Big Red House - Historic Bangor Home

Quiet single-level fully furnished house

Fairmount
10.0 out of 10, Exceptional, (52)
"Great location, Great Host and great Accommodations!"
United States
Tess K.
The price is AU$251
includes taxes & fees
15 Dec - 16 Dec
Quiet single-level fully furnished house

Gorgeous Waterfront Estate In Historic Bayside

Northport
10.0 out of 10, Exceptional, (76)
"This was a great place with great owners. Would recommend to anyone"
United States
John S.
Gorgeous Waterfront Estate In Historic Bayside

Charming Home Walk Downtown/Waterfront

Belfast
9.8 out of 10, Exceptional, (13)
"Easy walking distance to town. Perfect with our dog. Lovely home. "
United States
Ann L.
Charming Home Walk Downtown/Waterfront

35 Mi to Acadia: Rustic Retreat in Orland!

2.0 star property
Orland
6.0 out of 10, (2)
"Exactly what you think of a cabin in the Maine woods. Close to Bucksport. No wifi. Only got one channel on the rabbit ears for the TV, but many movies available to use on the dvd player. Dark outside at night. Quick response from property manager. Would stay there again. "
United States
Jayson
35 Mi to Acadia: Rustic Retreat in Orland!

Secluded Orland Cottage w/ Grill, Near State Parks

3.0 star property
Orland
Secluded Orland Cottage w/ Grill, Near State Parks

Charming 3-bedroom cottage in Hampden with AC, WiFi

2.0 star property
Hampden
9.6 out of 10, Exceptional, (19)
"Great for our dogs! Wonderful hospitality! Thank you Rebekkah!"
United States
Justine
The price is AU$318
includes taxes & fees
14 Dec - 15 Dec
Charming 3-bedroom cottage in Hampden with AC, WiFi

Middle of Everywhere - 4 BR Waterfront!

Prospect
10.0 out of 10, Exceptional, (3)
"House was clean. It had everything we needed. Owner is very responsive. We enjoyed our stay!"
United States
Al W.
Middle of Everywhere - 4 BR Waterfront!

NEW MaineStay Cottage #3 Full Kitchen + Fireplace in Hampden/Bangor

Hampden
10.0 out of 10, Exceptional, (45)
"Always a great place for overnight stayWe will often stay if we are coming up for a concertConvenient location "
United States
Todd A.
The price is AU$266
includes taxes & fees
21 Dec - 22 Dec
NEW MaineStay Cottage #3 Full Kitchen + Fireplace in Hampden/Bangor

PINE LODGE NORTHPORT MAINE FAMILY REUNIONS, WEDDING,RETREAT ACADIA BAR HARBOR

Northport
9.6 out of 10, Exceptional, (55)
"Easy Check in. Large kitchen and two large refrigerators were great for our large family. "
United States
Nelson G.
PINE LODGE NORTHPORT MAINE FAMILY REUNIONS, WEDDING,RETREAT ACADIA BAR HARBOR

Waterfront Hampden Home on Hermon Pond!

3.0 star property
Hampden
8.0 out of 10, Very good, (2)
"A beautiful and quiet spot on the water, only a few miles from town. We heard loons and saw a bald eagle grab a fish from the pond. The house itself was cozy, clean, and comfortable. "
United States
EMILY
Waterfront Hampden Home on Hermon Pond!

Maplewood Lakehouse in Newport

Newport
10.0 out of 10, Exceptional, (8)
"Maplewood Lakehouse was clean, spacious, accommodating, and everything our large group needed."
United States
Jane H.
Maplewood Lakehouse in Newport

MaineStay Cottage #5 With Fireplace & Fully Stocked Kitchen in Hampden/Bangor

Hampden
10.0 out of 10, Exceptional, (52)
"We enjoyed our stay, the cottage had everything we needed. "
United States
Gina C.
The price is AU$266
includes taxes & fees
14 Dec - 15 Dec
MaineStay Cottage #5 With Fireplace & Fully Stocked Kitchen in Hampden/Bangor

Bayside vista

Bucksport
10.0 out of 10, Exceptional, (15)
"We loved our stay in Bucksport. The apartment was comfortable, clean and had everything we needed - and the view could not be beat! "
United States
Allison M.
The price is AU$488
includes taxes & fees
22 Dec - 23 Dec
Bayside vista

Gorgeous estate overlooking Penobscot Bay

Lincolnville
9.8 out of 10, Exceptional, (66)
"We stayed with our extended family of 9 people and Suzanne’s house was absolutely perfect for us! Everything was clean, the beds were comfortable and the kitchen stocked better than mine at home! The house itself is spectacular. The enormous porch overlooking the bay was one of the most beautiful and relaxing setting I’ve ever experienced. We hope to be back soon. "
United States
Carrie K.
Gorgeous estate overlooking Penobscot Bay

NEW 2025 RV, 1 Bedroom WiFi AC in Serene Winterport with Coast and Bangor nearby

Winterport
10.0 out of 10, Exceptional, (3)
"Great place to stay"
United States
Aaron
NEW 2025 RV, 1 Bedroom WiFi AC in Serene Winterport with Coast and Bangor nearby

Mid-Coast Maine cabin less than an hour from Acadia NP! New Sauna! Cabin #3 Pine

Stockton Springs
10.0 out of 10, Exceptional, (8)
"Comfy and cozy. Perfect cabin feel. "
United States
Brigitte W.
Mid-Coast Maine cabin less than an hour from Acadia NP! New Sauna! Cabin #3 Pine
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 Jackson Hotel Reviews

Find out more about Jackson

Everything you need to know about Jackson 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 Jackson holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, 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 Jackson holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Jackson holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Jackson. 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Jackson 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 Jackson holiday rentals we have selected for you start as low as AU$251 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Jackson rentals

At Expedia, we put the best Jackson 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 Jackson 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 Jackson 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 Jackson. 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 Jackson?

Yes, there are holiday rentals close to the most popular sights in Jackson, or you can select a more secluded option if you're looking for a relaxing stay.

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

New listing. Charming 3-bedroom lake house in Orrington WiFi, Hot tub, and Sauna: This holiday home rental outside of Jackson offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

What can I see and do in Jackson?

Explore the area and family-friendly sights such as The Sports Arena, or get out into nature at a spot like Swan Lake. In the wider area, you’ll find Sandy Pond and Hermon Mountain.

What are holiday rentals like in Jackson?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Jackson. Holiday rentals offer extras such as kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, holiday rentals can offer a sense of seclusion away from shared hotel lifts and lobbies packed with people while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive option for families.