Town of Pines Guest Houses
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Guest Houses in Town of Pines

Luxury Guesthouse in private wooded setting in Grand Beach New Buffalo
New Buffalo MI
$398 nightly
The price is $398 total per night
$398 total
Jan 30 - Jan 31
Total with taxes and fees
When you stay at this guesthouse in New Buffalo, you'll be on a lake, within a 15-minute drive of Lake Michigan and Blue Chip Casino.
Pet friendly
Air conditioning

(2026 OPEN! ) Three Oaks Unit Steps To Downtown! 2 Night Summer Min!
Three Oaks MI
With a stay at this guesthouse in Three Oaks, you'll be within a 15-minute drive of Lake Michigan and Four Winds Casino New Buffalo.

(2026 OPEN!) Gorgeous Union Pier Home Close To Beach and Downtown!
Union Pier MI
When you stay at this guesthouse in Union Pier, you'll be near the beach, within a 15-minute drive of Lake Michigan and Four Winds Casino New Buffalo.

2026 OPEN! Three Oaks Multi Unit (2 Night Summer Min)
Three Oaks MI
Located in Three Oaks, this guesthouse is within a 15-minute drive of Lake Michigan and Four Winds Casino New Buffalo.

Elyon Hall CoachHouse, Indiana Dunes Nat’l Park, 10 min hike to Beach
Miller Beach IN
Located in Gary (Miller Beach), this guesthouse is steps from Lake Michigan and a 3-minute drive from Indiana Dunes National Park.

Cozy Couples Retreat in Beachwalk Resort w/ Hot Tub
Michigan City IN
When you stay at this guesthouse in Michigan City, you'll be near the beach, within a 5-minute drive of Lake Michigan and Blue Chip Casino.

Captain Whittaker Suite 2 bedroom, 2 baths
New Buffalo MI
$289 nightly
The price is $309 total per night
$309 total
Jan 31 - Feb 1
Total with taxes and fees
With a stay at this guesthouse, you'll be centrally located in New Buffalo, a 2-minute drive from Lake Michigan and 11 minutes from Four Winds Casino New Buffalo.

Galien Room Suite King size with Jacuzzi
New Buffalo MI
With a stay at this guesthouse, you'll be centrally located in New Buffalo, a 2-minute drive from Lake Michigan and 11 minutes from Four Winds Casino New Buffalo.

Beacons' Nest – Valpo U, Downtown & Dunes
Valparaiso IN
A stay at this guesthouse places you in the heart of Valparaiso, within a 5-minute drive of Chicago Street Theatre and Porter County Museum.

Chesterton “Golf View Estate” Midwest Great Lake Beaches & Trails Of The Dunes!
Chesterton IN
With a stay at this guesthouse in Chesterton, you'll be within a 10-minute drive of Indiana Dunes National Park and Portage Imagination Glen Park.

SS Post Boy Queen Suite with Jacuzzi
New Buffalo MI
With a stay at this guesthouse, you'll be centrally located in New Buffalo, a 2-minute drive from Lake Michigan and 11 minutes from Four Winds Casino New Buffalo.

Eber Knight Studio - King size with Jacuzzi
New Buffalo MI
$195 nightly
The price is $209 total per night
$209 total
Feb 2 - Feb 3
Total with taxes and fees
With a stay at this guesthouse, you'll be centrally located in New Buffalo, a 2-minute drive from Lake Michigan and 11 minutes from Four Winds Casino New Buffalo.
Hot Tub
Free WiFi
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.
Town of Pines Guest Houses essential information
Accommodation | 14 Guest Houses |
|---|---|
Lowest Price | $209 |
Highest Price | $398 |
Popular accommodation | Luxury Guesthouse in private wooded setting in Grand Beach New Buffalo, (2026 OPEN! ) Three Oaks Unit Steps To Downtown! 2 Night Summer Min!, (2026 OPEN!) Gorgeous Union Pier Home Close To Beach and Downtown!, 2026 OPEN! Three Oaks Multi Unit (2 Night Summer Min), Elyon Hall CoachHouse, Indiana Dunes Nat’l Park, 10 min hike to Beach, Cozy Couples Retreat in Beachwalk Resort w/ Hot Tub, Captain Whittaker Suite 2 bedroom, 2 baths, Galien Room Suite King size with Jacuzzi, Beacons' Nest – Valpo U, Downtown & Dunes, Chesterton “Golf View Estate” Midwest Great Lake Beaches & Trails Of The Dunes!, SS Post Boy Queen Suite with Jacuzzi, Eber Knight Studio - King size with Jacuzzi |
