Holiday rentals in Portland

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Top-rated holiday rentals in Portland

Guests agree: these stays are highly rated for location, cleanliness and more.

Guest favourite

Cabin in Cottontown

4.98 out of 5 average rating, 135 reviews

Candlelight -hiking, fishing, 30 min to Nashville

Welcome to Candlelight Cabin, tucked away at the trail head of the historic Wilkinson Farm, a private 100 acre retreat conveniently located 30 minutes North of Nashville. Enjoy miles of hiking trails, a fire pit, fishing pond, golf range and a spacious lawn for recreation. We provide firewood, fishing gear, trail maps and recommendations for nearby attractions and dining options. Candlelight Cabin has fast wifi, DVDs, fully stocked kitchen and laundry room. Event pavilion available on request.

12–19 Mar

$242 SGD per night
Guest favourite

Home in Franklin

4.91 out of 5 average rating, 208 reviews

Cozy Boho Country Bungalow in Central Franklin KY

Enjoy this newly renovated 1940’s, 1 bedroom bungalow during your stay to Franklin, KY. Peaceful and modern indoor and outdoor spaces create a perfect environment for your next work trip, date night or weekend away. Minutes from I-65, this retreat accommodates the perfect day trip to Nashville, Mammoth Cave, or Amish Markets. Scroll down to the bottom and click "contact host" to say hi and ask us any questions you may have about the space before booking. We are happy to help in any way we can!

13–20 Feb

$193 SGD per night
Guest favourite

Guest house in Portland

4.99 out of 5 average rating, 138 reviews

Howdie's Cottage near Nashville and Bowling Green

Our tiny studio guest cottage is located half way between Bowling Green,KY and Nashville,TN just 1.5 miles off I-65 @ exit 117. Private, beautiful farm views and convenient to everything Nashville and Southern KY has to offer. Enjoy Music city and all things Nashville. Head North for the day and visit Mammoth Caves or the Corvette Museum. Head back in the evening and we just might have a fire going in the fire pit! Short and long term guests welcome. Please inquire about long term pricing.

1–8 Jul

$117 SGD per night

Popular amenities for Portland holiday rentals

Stay near Portland's top sights

Food Lion3 locals recommend
El Azteca3 locals recommend
Senor Fajita's4 locals recommend

Other great holiday rentals in Portland

Guest favourite

Home in Scottsville

4.94 out of 5 average rating, 110 reviews

The Crafted House

3–10 Oct

$178 SGD per night
Guest favourite

Tiny home in Goodlettsville

4.89 out of 5 average rating, 170 reviews

Herondale at Flat Ridge Farms -30 min to Nashville

8–15 Sep

$220 SGD per night
Guest favourite

Farm stay in Scottsville

4.99 out of 5 average rating, 187 reviews

Flower Farm Modern Loft Retreat - Mammoth Cave

20–27 Jun

$164 SGD per night
Guest favourite

Cottage in Springfield

4.83 out of 5 average rating, 105 reviews

The Cottage at Birdsong Farm

4–11 May

$173 SGD per night
Guest favourite

Guest house in Scottsville

4.98 out of 5 average rating, 111 reviews

Adorable Guesthouse #2 Close to Barren River Lake

11–18 Jun

$123 SGD per night
Guest favourite

Treehouse in Springfield

4.9 out of 5 average rating, 465 reviews

Unique Treehouse With Spectacular View.

18–25 Oct

$244 SGD per night
Guest favourite

Home in Portland

5.0 out of 5 average rating, 27 reviews

Romantic cozy cottage

31 Aug – 7 Sep

$164 SGD per night
Guest favourite

Home in Portland

4.94 out of 5 average rating, 52 reviews

The Getaway.Need a break from big city living?

16–23 Mar

$134 SGD per night
Guest favourite

Home in Portland

5.0 out of 5 average rating, 45 reviews

The Yellow House - Hidden Gem in heart of Portland

12–19 Sep

$340 SGD per night
Guest favourite

Cottage in Cross Plains

5.0 out of 5 average rating, 63 reviews

The Magnolia Cottage ~ The Great Outdoors

23–30 Aug

$209 SGD per night
Guest favourite

Cabin in Cross Plains

4.98 out of 5 average rating, 83 reviews

"River House" Log Cabin Nestled near the Red River

31 May – 7 Jun

$202 SGD per night
Guest favourite

Cabin in Russellville

4.98 out of 5 average rating, 41 reviews

Cozy Cabin with Private Walking Trail

16–23 Aug

$132 SGD per night

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