Holiday Rentals in Grimsley

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Grimsley holiday rentals

Wyndham Resort at Fairfield Glade - 2 Bedroom Condo

Wyndham Resort at Fairfield Glade - 2 Bedroom Condo
Fairfield Glade
9.6 out of 10, Exceptional, (213)
"We would stay here again. "
United States
Ginger T.
Wyndham Resort at Fairfield Glade - 2 Bedroom Condo

Romantic Secluded Cabin For Two

Romantic Secluded Cabin For Two
Monterey
9.8 out of 10, Exceptional, (295)
"Nice secluded cabin."
United States
TINA K.
Romantic Secluded Cabin For Two

Lake Front unit ready 4 you! - sleeps 12 in beds, w/king bed, WiFi, pets

Lake Front unit ready 4 you! - sleeps 12 in beds, w/king bed, WiFi, pets
Crossville
9.8 out of 10, Exceptional, (205)
"Second stay here. Great location with good amenities. Owners were communicative and prompt. "
United States
Johanna G.
Lake Front unit ready 4 you! - sleeps 12 in beds, w/king bed, WiFi, pets

The Holiday Hutt at Dale Hollow Lake-Close to Sunset, Bball Court, Movie Theater

The Holiday Hutt at Dale Hollow Lake-Close to Sunset, Bball Court, Movie Theater
Monroe
10.0 out of 10, Exceptional, (14)
"Being able to put all 20 of us in one beautiful place with plenty of things to do for the younger grandchildren, teenagers and adults. This place is ideal for being a short distance from Sunset Marine and Dale Hollow Lake. Thank you, Michael"
United States
Bob D.
The Holiday Hutt at Dale Hollow Lake-Close to Sunset, Bball Court, Movie Theater

Secluded and Romantic Cabin ~ 35 Private Secluded Acres ~ Jacuzzi Tub!

Secluded and Romantic Cabin ~ 35 Private Secluded Acres ~ Jacuzzi Tub!
Monterey
10.0 out of 10, Exceptional, (222)
"Very nice and peaceful "
United States
gail l.
Secluded and Romantic Cabin ~ 35 Private Secluded Acres ~ Jacuzzi Tub!

Holpps Pine Ridge Lake tiny house B

Holpps Pine Ridge Lake tiny house B
Monterey
9.6 out of 10, Exceptional, (81)
"Quiet, family friendly lake with plenty to do: swimming, fishing, boating and plenty to do not far away."
United States
Steve
Holpps Pine Ridge Lake tiny house B

Peaceful cabin in secluded mountain spot beside a picturesque creek

Peaceful cabin in secluded mountain spot beside a picturesque creek
Wilder
9.8 out of 10, Exceptional, (58)
"Loved watching the stars at night, easy driveway was a plus. "
United States
Isabella S.
Peaceful cabin in secluded mountain spot beside a picturesque creek

Lakefront, Gas Firepit. Hot Tub. Private Dock. Pup Friendly

Lakefront, Gas Firepit. Hot Tub. Private Dock. Pup Friendly
Jamestown
10.0 out of 10, Exceptional, (119)
"Beautiful and relaxing, All the little touches made our stay special. Would definitely recommend!"
United States
JenniferAnn S.
Lakefront, Gas Firepit. Hot Tub. Private Dock. Pup Friendly

Cozy 2 bedroom cabin nestled in wooded hideaway

Cozy 2 bedroom cabin nestled in wooded hideaway
Monterey
9.0 out of 10, Wonderful, (23)
"We was out for work, this place gave us peace after a long day of work great place to stay."
United States
jose c.
Cozy 2 bedroom cabin nestled in wooded hideaway

Fairfield Glade condo with King size bed, pet friendly and WiFi

Fairfield Glade condo with King size bed, pet friendly and WiFi
Crossville
9.8 out of 10, Exceptional, (65)
"Enjoyed Fairfield Glades a lot. Plenty of nice trails in the area."
United States
Doug W.
The price is €215
includes taxes & fees
13 Jan - 14 Jan 2026
Fairfield Glade condo with King size bed, pet friendly and WiFi

Cabin on 6 acres with horse barn. Pasture and Woodland views. Trailheads abound.

Cabin on 6 acres with horse barn. Pasture and Woodland views. Trailheads abound.
Jamestown
9.8 out of 10, Exceptional, (28)
"Beautiful, quiet property off a dead-end road. Owners were great to work with. "
United States
Betsy W.
Cabin on 6 acres with horse barn. Pasture and Woodland views. Trailheads abound.

🔚 END Unit in ❤️Fairfield Glade- w/King bed; WiFi-2 showers

🔚 END Unit in ❤️Fairfield Glade- w/King bed; WiFi-2 showers
Crossville
9.4 out of 10, Exceptional, (197)
"Great place to stay."
United States
Cameron B.
The price is €212
includes taxes & fees
13 Jan - 14 Jan 2026
🔚 END Unit in ❤️Fairfield Glade- w/King bed; WiFi-2 showers

2 bedroom 1.5 bath in Fairfield Glade near the community center!

2 bedroom 1.5 bath in Fairfield Glade near the community center!
Crossville
9.4 out of 10, Exceptional, (33)
"Nice well maintained property, perfect for our stay"
United States
Patrick
The price is €196
includes taxes & fees
15 Dec - 16 Dec
2 bedroom 1.5 bath in Fairfield Glade near the community center!

Family Cabin on Clear Creek

Family Cabin on Clear Creek
Monterey
9.6 out of 10, Exceptional, (45)
"Great stay. The property was amazing. 10/10 would stay again. "
United States
Nick S.
Family Cabin on Clear Creek

Comfy condo! Wilshire area of Fairfield Glade: King Bed, WiFi and more!

Comfy condo! Wilshire area of Fairfield Glade: King Bed, WiFi and more!
Crossville
9.6 out of 10, Exceptional, (193)
"Thank you for your assistance and understanding over our stay"
United States
Alyssa W.
The price is €213
includes taxes & fees
15 Dec - 16 Dec
Comfy condo! Wilshire area of Fairfield Glade: King Bed, WiFi and more!

Your Own Private Lake ~ Secluded Cabin In The Woods ~ Romantic Retreat!

Your Own Private Lake ~ Secluded Cabin In The Woods ~ Romantic Retreat!
Monterey
9.8 out of 10, Exceptional, (163)
"Wonderful, quiet, and serene location. Very peaceful! Felt right at home. Husband and son fished almost every morning and evening Great hosts!"
United States
Jennifer W.
Your Own Private Lake ~ Secluded Cabin In The Woods ~ Romantic Retreat!

Luxurious Log Cabin Retreat: Your Private Getaway

Luxurious Log Cabin Retreat: Your Private Getaway
Monterey
10.0 out of 10, Exceptional, (3)
"The home and grounds were beautiful! The hosts have thought of all the necessary stuff plus so much more. We only wish we had been in the area longer."
United States
Patience A.
The price is €281
includes taxes & fees
16 Dec - 17 Dec
Luxurious Log Cabin Retreat: Your Private Getaway

Cozy 1-bedroom house in charming Allardt with AC, WiFi

Cozy 1-bedroom house in charming Allardt with AC, WiFi
Allardt
10.0 out of 10, Exceptional, (12)
"Clean, comfortable, well located, with a great host who made everything easy start to finish. Would definitely stay here again."
United States
Robert M.
Cozy 1-bedroom house in charming Allardt with AC, WiFi

The Treehouse - TN Honeymoon Cabin - HOT TUB - in BSF!!!

The Treehouse - TN Honeymoon Cabin - HOT TUB - in BSF!!!
Fentress County
10.0 out of 10, Exceptional, (19)
"Great little place to stay! "
United Kingdom
Kristen M.
The Treehouse - TN Honeymoon Cabin - HOT TUB - in BSF!!!

Cabin in the Big South Fork/Pickett State Park Area.

Cabin in the Big South Fork/Pickett State Park Area.
Jamestown
10.0 out of 10, Exceptional, (183)
"Excellent stay in a great location."
United States
Yaroslav
Cabin in the Big South Fork/Pickett State Park Area.
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Grimsley Hotel Reviews

Find out more about Grimsley

Everything you need to know about Grimsley 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 Grimsley 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 Grimsley holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Grimsley holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Grimsley. 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 Grimsley 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 Grimsley holiday rentals we have selected for you start as low as €196 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Grimsley rentals

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

Yes, there are holiday rentals close to the most popular sights in Grimsley, 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 Grimsley has to offer?

Fairfield Glade condo with King size bed, pet friendly and WiFi: This holiday home rental outside of Grimsley offers a patio, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

What can I see and do in Grimsley?

While you're exploring the area, Obed Wild & Scenic River and Pogue Creek Canyon State Natural Area are a couple of picturesque spots to get outside and enjoy nature. In the wider area, you’ll find Jamestown Town Hall and Fentress County Public Library.

What are holiday rentals like in Grimsley?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Grimsley. Holiday rentals provide amenities such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from shared hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for a family getaway.