828-526-9999
Highlands Vacation Rentals Logo
Highlands Vacation Rentals Logo
828-526-9999

Overlook Loft at Oak over Main

Overlook Loft at Oak over Main

Overlook Loft at Oak over Main

New for 2026 !
2 Bedrooms 2 Bathrooms Sleeps 4 Highlands

Bedroom 1

1 King

Bedroom 2

1 King

Overlook at Oak Over Main is a spacious two-bedroom, two-bathroom Loft with views of Highlands Main Street. With earthy, eclectic interiors inspired by the Blue Ridge Mountains, all of Oak Over Main’s lofts feel cozy, inviting, and refined. Overlook features a large kitchen with island, and the largest private deck on the property with both an outdoor dining table and Adirondack seating area. Perfect for couples or groups up to four, you’ll enjoy walkable access to all of downtown Highlands’ shopping and dining.

Oak Over Main is a brand new collection of four luxury lofts on a rooftop in the center of downtown Highlands. Each loft features high-end finishes, heated bathroom floors, Le Labo bath amenities, Nespresso coffee, full kitchens, NetZero electric fireplaces, Wi-Fi, Samsung Smart TVs, private rooftop decks with outdoor heaters, and exclusive access to Oak Over Main’s rooftop garden patio, with a bird’s-eye view of Main Street.


** Please be advised that the *Admin Fee * covers many admin costs associated with the reservation. However, If you wish to avoid much of this fee, do not put in payment information. You may still place your reservation but will need to call the office at 828-526-9999 **

Essentials

  • Air Conditioning
  • Living Room
  • Kitchen
  • Bed Linens
  • Linens Provided
  • Extra Pillows & Blankets
  • Towels
  • Hangers
  • Heating
  • Hot Water
  • Shampoo
  • Free Wifi
  • Private Entrance
  • Clothes Steamer
  • Heated Bathroom Floors
  • Private Terrace/Patio
  • Smart TV's

Home Safety

  • Carbon Monoxide Detector/Alarm
  • Smoke Detector
  • Smart Door Locks

Kitchen

  • Dishes & Silverware
  • Dishwasher
  • Oven
  • Electric Cooktop
  • Microwave
  • Refrigerator
  • Dining table
  • Coffee Maker

Location

  • Downtown
  • Walk-to-Town

Facility

  • Street Parking

Outdoor

  • Balcony

Entertainment

  • Smart TV

Fireplaces

  • Indoor Electric Fireplace

Leisure

  • Antiquing
  • Horseback Riding
  • Outlet Shopping
  • Shopping
  • Wildlife Viewing

Local

  • Hospital
  • Fitness Center

Sports

  • Fishing
  • Fishing - Fly
  • Hiking
  • Hunting
  • Ice Skating
  • Mountaineering
  • Rock Climbing
  • Skiing
  • Snowboarding
  • Swimming
  • Water Tubing
  • Whitewater Rafting

Themes

  • Family
  • Couples
  • Groups
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December 2025
S M T W T F S
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$739
20
$924
21
$880
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28 29 30 31
$990
     
January 2026
S M T W T F S
        01
$992
02
$961
03
$960
04
$755
05
$718
06
$706
07
$751
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$775
09
$804
10
$808
11
$781
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$734
13
$723
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$746
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$809
16
$944
17
$956
18
$975
19
$853
20
$846
21 22
$858
23
$905
24
$921
25
$839
26
$847
27
$845
28
$827
29
$863
30
$892
31
$898
February 2026
S M T W T F S
01
$813
02
$799
03
$806
04
$833
05
$864
06
$917
07
$933
08
$862
09
$812
10
$852
11
$832
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$876
13
$1000
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$1006
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$964
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$856
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$848
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$817
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$862
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$925
21
$934
22
$849
23
$792
24
$783
25
$787
26
$816
27
$907
28
$896
March 2026
S M T W T F S
01
$795
02
$789
03
$788
04
$783
05
$817
06
$855
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$865
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$819
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$804
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$798
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$796
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$827
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$897
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$959
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$961
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$1037
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$938
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$939
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$889
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$854
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$804
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$854
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$898
27
$946
28
$911
29
$873
30
$807
31
$806
       
April 2026
S M T W T F S
      01
$880
02
$880
03
$936
04
$946
05
$944
06
$880
07
$880
08
$880
09
$893
10
$930
11
$950
12
$880
13
$919
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$921
15 16
$904
17
$924
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$924
19
$880
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$880
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$880
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$880
23
$895
24
$934
25
$932
26
$880
27
$880
28
$880
29
$880
30
$930
   
May 2026
S M T W T F S
          01
$954
02
$952
03
$880
04
$880
05
$880
06
$880
07
$880
08
$939
09
$946
10
$915
11
$985
12
$994
13
$948
14
$1027
15
$1069
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$1057
17
$968
18
$880
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$880
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$887
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$902
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$1110
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$1133
24
$1112
25
$1076
26
$1028
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$1121
28
$1283
29
$1532
30
$1524
31
$1416
           
June 2026
S M T W T F S
  01
$977
02
$907
03
$936
04
$942
05
$1007
06
$1014
07
$976
08
$939
09
$940
10
$973
11
$1044
12
$1123
13
$1122
14
$1062
15
$1041
16 17 18
$1119
19
$1171
20
$1142
21
$1051
22
$1027
23
$1026
24
$1079
25
$1171
26
$1235
27
$1160
28
$1076
29
$1052
30
$1064
       
July 2026
S M T W T F S
      01
$1167
02
$1563
03
$1584
04
$1572
05
$1390
06
$1295
07
$1382
08
$1325
09
$1283
10
$1370
11
$1459
12
$1418
13
$1245
14 15
$1202
16
$1165
17
$1228
18
$1214
19
$1103
20
$1085
21
$1087
22
$1117
23
$1166
24
$1241
25
$1247
26
$1389
27
$1262
28
$1227
29
$1111
30
$1153
31
$1180
 
August 2026
S M T W T F S
            01
$1181
02
$1067
03
$1048
04
$1041
05
$1028
06
$1096
07
$1151
08
$1148
09
$1094
10
$1010
11
$1005
12
$1073
13
$1060
14
$1095
15
$1105
16
$1016
17
$999
18
$996
19
$1043
20
$1105
21
$1289
22
$1232
23
$1078
24
$1002
25
$966
26
$962
27
$992
28
$1082
29
$1112
30
$1022
31
$962
         
September 2026
S M T W T F S
    01
$939
02
$938
03
$1004
04
$1222
05
$1222
06
$1215
07
$926
08
$894
09
$899
10
$951
11
$1014
12
$1008
13
$924
14
$991
15
$1188
16 17
$1031
18
$1046
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$1032
20
$1027
21
$947
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$912
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$904
24
$960
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$1078
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$1065
27
$928
28
$909
29
$921
30
$950
     
October 2026
S M T W T F S
        01
$1005
02
$1165
03
$1177
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$1044
05
$954
06
$911
07
$963
08
$1254
09
$1439
10
$1451
11
$1455
12
$1232
13
$1232
14
$1180
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$1142
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$1258
17
$1275
18
$1028
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$1022
20
$1077
21
$1022
22
$1063
23
$1168
24
$1158
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$970
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$935
27
$1042
28
$963
29
$1019
30
$1092
31
$1083
November 2026
S M T W T F S
01
$947
02
$899
03
$881
04
$914
05
$960
06
$1075
07
$1073
08
$953
09
$882
10
$1073
11
$1079
12
$1251
13
$1307
14
$1339
15
$1134
16
$920
17
$965
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$1013
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$1059
20
$1077
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$1008
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$922
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$928
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$973
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$1220
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$1224
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$1227
28
$1227
29
$922
30
$931
         
December 2026
S M T W T F S
    01
$967
02
$938
03
$992
04
$1090
05
$1013
06
$903
07
$876
08
$870
09
$861
10
$899
11
$942
12
$965
13
$939
14
$940
15
$945
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$919
17
$939
18
$961
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$1003
20
$987
21
$982
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$993
23
$1130
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$1130
25
$1131
26
$1130
27
$1157
28
$1157
29
$1157
30
$1194
31
$1194
   
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